CHIRALPAK® ZWIX(+) - 株式会社ダイセル CPIカンパニー
Contents
1. gt pH9 0 pH7 0 25 3 3 2 pH2 0 HPLC2. 10 20mM 100mM LC MS 2 2 gt gt NIN DMOA TFA OA HFBA
3. lt pH2 0 pH 20mM gt pH9 0 pH7 0 25 15 16
4. 3 7 7 1 1 7 1 2 7 1 3 7 1 5 7 1 6 7 1 7 7 1 8 7 2 7 2 1 7 2 2 7 2 3 72 4 2 2 5 200205005 2 7 3 CHIRALPAKAGP 7 3 1 7 3 2 pH 7 3 3 7 3 4 7 3 5 7 3 6 AEN 7 1 1 qa1
5. HPLC ea 3 1 1 1 3 1 1 2 3 1 1 3 4 1 1 4 4 1 1 5 4 1 1 6 4 1 1 7 4 1 2 5 1 2 1 5 1 2 2 6 1 2 3 8 1 3 10 1 3 1 10 1 3 2 10 1 3 3 11 1 4 12 1 5 13 1 5 1 13 1 5 2 13 1 6 14 1 6 1 14 1 6 2 15 1 7 16 1 7 1 16 1 7 2 1009 16 1 7 3 IA
6. 2 1 1 7 No pH7 0 1 2 HPLC p 8 3
7. 4 6mm 7 CHIRALPAK IA CHIRALPAK ID CHIRALPAKY7IA 3 CHIRALPAKYIB IB 3 CHIRALPAKY IE IE 3 CHIRALPAK ID 3 CHIRALPAK IC IC 3 HIRALPAK IF IF 3 Ds 0 5 mLmin 30 0 5 mLmin 30 1 0 mL min 30 NN DMF N N DMF 0 3 mL min 180 0 4 mL min 240 48 al 0 3 mL min 50 0 05 mL min 600 4 6mm
8. 3 10 20 3 1 8 pH7 DMF DMSO THF HPLC
9. 9 LC MS 50mM RR 20mM NN CHIRALPAK IA IA 3 ID ID 3 a 24 IE IE 3 IF IF 3 pH2 0 50nmM 100mM KPF NaPF pH2 0 a pH2 0 100mM KPF NaPF CHIRALPAK IB IB 3 IC IC 3 pH2 0 pH2 0 100mM KPF NaPF 0 5um
10. 2 1 3 n 2 t MTBE MTBE 50vol CHIRALPAK AD H AD 3 AS H AS 3 AY H AY 3 AZ H AZ 3 CHIRALCEL OD H OD 3 0OJ H 0J 3 OZ H OZ 3 OX H OX 3 2 1 4 Ra Vd 2 1 5
11. 4 5B 0 5 10 15 20 25 30 35 40 0 5 10 15 20 25 30 0 5 10 15 20 25 30 TemDp 10C 25 yy A400C O Column CHIRALPAKY IA OO 4 6mmX 250mm Mobile phase n Hex IPA TFA 95 5 0 1 v v v Ketoprofen Flow rate 1 0mL min n Hex n IPA 2 TFA 1 3 3 n iso n 2 1 1 2 59
12. p 11 5 1 20 20 Column CHIRALPAK IA 6 72 L COOH 22 53 4 6mm Xx 250mm 7 41 Flow rate 1 0mL min Temp 25 Ketoprofen 0 4 9 12 16 20 0 5 10 15 20 25 30 n Hex IPA TFA 80 20 0 1 v v v n Hex IPA TFA 95 5 0 1 v v v n Hex n IPA 2 TFA 1 3 2 0 40 pH7 5 40 pH7 5 25
13. 2 n n 5 5 gt gt gt t gt n om EE gt gt gt gt gt gt MTBE 1 CH CN 100 CH CN EtOAc 70 30 v v 4 m 1 Aminoglutethimide CH CN EtOAc 40 60 v v Column CHIRALPAK IA
14. p35 p35 p35 17 CHIRALPAK AD RH 60 40 v v CHIRALPAKY AD 3R CHIRALPAMKC AS RH 60 40 v v CHIRALPAMK AS 3R 50 50 v v CHIRALPAK AY RH 30 70 v v CHIRALPAMK AY 3R CHIRALPAMK AZ RH 50 50 v v CHIRALPAK AZ 3R CHIRALCEL OD RH 60 40 v v CHIRALPAK OD 3R CHIRALCEL 0J RH 80 20 v v CHIRALPAK 0J 3R CHIRALCEL OX RH 30 70 v v CHIRALPAK OX 3R CHIRALCEL 0Z RH 40 60 v v CHIRALPAMK OZ 3R
15. gt 0 0 2mL min 2 n 50 50 v v H VTAMIN 2 1 5 2 1 lt 1 gt CROWNPAK CR D L CROWNPAK CR L D 250C HCIO aq pH 1 5 CH CN 80 20 0 2mL min UV HCOOHaq pH1 8 2 0 CH CN 80 20 10070 0 2mL min MS 2 lt K2 Ti or kK2 lt 2 k2 lt 2 MS UV pH HCIO aq pH1 0 1 2 EE
16. 0 5 m 2 1 6 1 2 2 1 7 p 25 2 2 2 2 2 n
17. 11 n 0 1 0 1 KW 0 5 0 5 1 DEA MEA nh MEA 29 CHIRALPAK AZ AZ 3 Column CHIRALPAKY AD 4 6mmxX 250mm Flow rate 1 0mL min Temp 40 Detect UV 254nm 1
18. THF MTBE t DMF N N DMAc NIN DMSO UV RI UV RI UV U Uetector Rolariaeter O0 13 8 UV 1 1 5 1 5 1 0 5mL minX30
19. 3 2 3 2 1 p 32 3 3 1 p 32 15 p 35 3 4 16 p 32 15 3 4
20. o kK Rs Ps IC ID IF AD OD trans Stilbene oxide to 1 3 5 Tri tertbutylbenzene gt
21. 0 19 DEA n Hex IPA DEA DEA TFA DEA TFA DEA nrHex IPA n Hex IPA TFA Es Bm ms 2 m 9 ei a After flushing with n Hex IPA 9 1 0 1 TFA After flushing with n Hex IPA 9 1 0 1 TFA analyzed with n Hex IPA 9 1 analyzed with n Hex IPA 9 1 0 1 DEA YVANI LV NI 5
22. HPLC 7 1 3 2 gt 7 1 4 00081 00081 9
23. 0 5um 80 20 v v pH pH gt pH CROWNPAK CR I CR I
24. _ 62 0 1920 0 0 5 ADscisic acid Pheniramine AA S 8 IPA 95 5 AA 4 5 IPA 9575 ss CO 1o 12 14 16 18 min 40 AA 4 5 IPA 98 2 aa 9 ws 10 At 6 3 1 5 15 min 2s AA S 8 IPA 97 3 a AA 4 5 CH CN 95 5 CO UL 8 AA 5 8 IPA 95 5 5 AS AA 3 8 IPA 98 2 1 2 k 15 7 3 4 CHIRALPAK AGP UN HexoDarbital NN WI 2 PnenoxyproDionic acid T
25. 8 3 um NN 2 1 21 2 1 1 21 2 1 2 2 1 3 22 2 1 4 2 1 5 22 2 1 6 22 2 1 7 2 2 2 23 2 2 1
26. 16 3 3 3 3 1 15 15 pH9 0 20mM 0 DD A Et DEA 15 16 3 3 2 16
27. 50mM 20mM CHIRALPAK AD RH AD 3R pH2 0 pH9 0 AS RH AS 3R AY RH AY 3R AZ RH AZ 3R pH2 0 50nmM 100mM KPF NaPF pH2 0 2 z pH2 0 CHIRALCEL OD RH OD 3R 7 100mM RP NaPF pH2 0 OJ RH OJ 3R OX RH OX 3R 7 0Z RH OZ 3R pH2 0 100mM KPF NaPF 0 5um 17
28. p 24 2 2 2 1 p 24 3 1 p 26 2 3 2 V 2 2 2 TFA DEA MEA EDA 0 1
29. pH6 0 10 0 4 pH k pH pH pH2 0 9 0 i ri ee F 3 0 00 5 6 9 10 ll pH PH pH CHIRALPAK AD RH 20mM 60 40 v v 0 5ml min 95 UV 220nm 4
30. NG 2 4 2 YVANI LV NI7
31. 18 _ 5 4 1 1 7 7 19 _ 5 4 2 6 6 606 E 2 51 1 7 8 19 5 4 3 51 1 7 9 19 _ 61 3 zkCak dC _ 6 1 1 3 2 1 1 21 _ 6 1 2 53 2 1 2 22 6 1 3 53 2 1 3 6 1 4 53 2 1 4 2 6 2 54 2 1 5 0 0 0 0 0 0 22 _ 6 2 1 54 216 22 622 5 217 623 55 _ 22 23 6 2 4 LC MS 56 2 2 1 23 6 3 CHIRALPAK ZWIX 56 2 2 2 24 6
32. 2 20vol9 MS CHIRALPAK ZWIX CHIRALPAK ZWIX 50mM FA 25mM DEA LC MS DEA LC MS 25mM 25mM in MeOH H 0 98 2 VV 1 9 MeOH CH CN H 0 49 49 2 v v v 50mM 25mM DEA 2 MeOH THF H 0 49 49 2 v v v 50mM 25mMDEA
33. _ 61 3 _ 6 1 2 _ 6 1 3 3 _ 6 14 53 _ _ 6 2 _ 62 1 1 54 _ 6 22 5 _ 62 3 5 _ 63 CHIRALPAK ZWIX _ 56 _ _ 63 1 56 6 3 2 6 _ 63 4 2 57 _ 63 5 57 _ 63 6 57 6 1 4 6 1 1 CHIRALPAK ZWIX SS ACHSA quinine a 3 0 QUININE DERIVED 8S 9R 100 ZWIX ll 2 CROWNPAK ZWIX ds 2 R R ACHSA quinidine QUININE DERIVED 8R 95 3 um
34. 5 4 3 7 CROWNPAK CR CR 100 10070 85715 CROWNPAK CR CR 15 gt pH 1 0 2 0 pH9 0 pH pH
35. 3 PO Column CHIRALCEL OD Eluent n Heptane 2 BIOBSROIMINIIOIO3G6IIGBGG 100 1 0 1 Flow rate 1 0mL min Det UV254nm Temp 25 4 k a k 2 o MM 0 100 200 300 400 2 00 700 0 100 200 300 400 500 H O mg L trans Stilbene Oxide 1 0mL min CHIRALCEL OD H 25 n Hex IPA 90 10 VV UV254nm 4 6
36. HPLC Rinse Solvent for Loop Ethanol Mobile Phase 8 lbuprofen 3 NE et 3 Ibuprofen
37. 7 2 1 10mM pH 5 8 2 95 5 v v 7 2 2 10mM 1L CH COONH 99 770 8mg HPLC 800mL 20 25 pH 0 22 um 1L 1L pH OO OLED 7 2 3
38. 1 Te EN i Os YY ee SE II LC i lt a 4 2 a Ni S
39. 17 1 7 4 IB 17 1 7 5 18 1 7 6 18 1 7 7 19 1 7 8 19 1 7 9 19 1 1 1 CHIRALPAK IA CHIRALPAK IA 3 CH A Amylose tris 3 5 dimethylphenylcarbpamate Amylose Jerivall IA5Uum IA 33um immobilized to silica gel R CHs IA nm 90 10 v v IA 3 n 2 90 10 v v CHIRALPAKY TB CHIRALPAKY IB 3 CHs Cellulose tris 3 5 dimethylphenylcarbamate llulose derivatiua IB5um IB 33um immobilized to silica gel CHs IB n 2 95 5 v v IB 3 n 2 90 10
40. 2 p 32 15 16 p 34 MTBE t 3 1 4 pH7 0 2 1 5 0 5u m
41. 5 1 3 CROWNPAK CR CR I HPLC THF CROWNPAK CR I CR I 2 H NI 5 1 4 CH CN MeOH EtOH IPA THF AT
42. pH 3 4 6 8 oo Nl 8 HBO Na B O U CHIRAILPAK AD RH miM phH 9 0OWyW mmin UV POmm 5 4 Trouble 4 6 41 4 7 41 4 1
43. CROWNPAK CR CROWNPAK CR 5 4 1 CROWNPAKY CR 18 crown 6 ether Lm 95 5 v v CROWNPAKY CR R 18 crown 6 ether Um 95 5 v v 5 4 2 X 4 0X150mm 0 15 MPa 153 kgf cm2 pH pH 1 0 9 0 0 HPLC
44. 5X50cm IA 3 2 1mm EtOH 0 1mL minX30min DMF 0 08mL minX240min EtOH 0 1mL minX30min IA MeOAc N 4 lt Column CHIRALPAK IA 250mmX 4 6mm Mobile phase n Hex EtOH 90 10 V V _ Flow rate 1 0mL min CH CN n Hex nh EtOH Temp 25 1 5 2 n nh 2 90 10 v V 3 1 6
45. Mobile phase 100 O a 4 Benzoyloxy 2 azetidinone 0 WI Column CHIRALPAK IA 4 6mm 250mm Flow rate 1 0mL min Temp 25 Mobile phase 100 P HH Glutethimide 3 i 1 Column CHIRALPAK IA 4 6mmx 250mm Flow rate 1 0mL min Temp 25 Mobile phase 100 Thalidomide 1 EL IN Column CHIRALPAK IA 4 6mm 250mm Flow rate 1 0mL min Temp 25 Mobile phase TFA 100 0 1 v v Column CHIRALPAK IA 4 6mmx 250mm Flow rate 1 0mL min Temp 25 MTBE t EDA TFA Mobile phase MTBE EDA 100 0 1 Vv OH CT Alprenolol 1 lira Column CHIRALPAKY IB 4 6mmx 250mm Flow rate 1 0mL min Temp 25 Mobile phase 100 N a Praziquantel Column CHIRALPAK IC 4 6mm x 250mm Flow rate 1 0mL min Temp 25 C 1 7 3 IA IA Methaqualone
46. Go Amylose tris 3 chloro 4 methylphenylcarbamate SW 6 AZ H 5 um AZ 33um Amylose derivative N AZ H n 2 90 10 v v alca OS H AZ 3 n 2 90 10 v v CHIRALCEL OD H CHIRALCEL OD 3 OR Cellulose tris 3 5 dimethylphenylcarbamate OD H5um OD 33um V 2 1 2 CHIRALPAK AD H AD 3 AS H AS 3 AY H AY 3 AZ H AZ 3 CHIRALCEL OD H OD 3 0OJ H 0J 3 0Z H 0Z 3 OX H OX 3 10 21 20 mim 4 6mm 30MPa 305kgf cm2 0 1 0 2mL min 0 5 1 0mL min 0 40 HPLC
47. gt MeOAC 5 P13 A EtOH 6 n Hex IPA 0 196TFA n Hex IPA n Hex IPA TFA
48. 37 3 4 6 7 EEC 3 1 1 CHIRALPAKY AD RH CHIRALPAK AD 3R OD 3R 60 40 v v CHIRALCEL OJ RH CHIRALCEL OJ 3R Cellulose tris 4 methylbenzoate OJ RH 5um OJ 3R 3um 0J RH 80 20 v v OJ 3R 80 20 v v CHIRALCELY OZ RH CHIRALCEL OZ 3R Cellulose tris 3 chloro 4 methylphenylcarbamate OZ RH 5um OZ 3R 3 um 0Z RH 40 60 v v OZ 3R 40 60 v v CHIRALCELY OX RH CHIRALCEL OX 3R Cellulose tris 4 chloro 3 methylphenylcarbamate OX H 5um OX 3 3um OX RH 30 70 VV OX 3R 30 70 v v O RO OR n Cellulose derivative silica gel 6 n Cellulose derivative silica gel DE 0 O 5e
49. tein 2 75 25 v v 4mm 0 3mL min HPLC 2 90 10 v v 2 85 15 v v 30 7 3 CHIRALPAK AGP 7 3 1 10mM pH5 8 2 95 5 EI N B A B N RA ENN k gt 15 TE 1 2 lt k 15 QA pH4 Pl mnt Rs 0 oo a 12 0 15 Ly CH CN EtOH MeOH 15 yy
50. 0 40 Column CHIRALPAK AD F 46mm x 250mm Mobile phase n Hex IPA AcOH 90 10 0 1 V V V COOH Flow rate 1 0mL min Flurbiprofen 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 19 1 2 3 4 5 6 7 8 9 10 11 12 13 14 19 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 min min min Temp 10C 25 Cy 40C n Hex nh IPA 2 AcOH 2 3 3 n iso n 2
51. CROWNPAK CR I CR I K gt II a 0 5 um 0 2mL min 2 95 5 v v 5 1 5 n
52. 2 Max 9096 3 1 20 4 4 5 ee n Hex THF n Hex n Hex CHCI a 0 a 70 30 50 50 30 70 100 0 100 0 a 99 1 50 50 99 1 50 50 60 40 100 0 85 15 0 100 85 15 0 100 WV WV v v v v v v 1 0mL min 25 X 4 6mmx250mm 1 4 nh Hex nh EtOH MeOH IPA 2 MTBE t CH CI THF CHCI CH CN p 8 1 2 3
53. t MTBE 14 HPLC 1 1 4 pH7 0 a 1 1 5 0 5 m 1 1 6 1
54. 46mmX 250mm Flow rate 1 0mL min N Oo 4 Temp 25 Miconazole MTBE MeOH Additive 94 6 0 1 v v v MTBE tt MeOH 1 2 3 TFA DEA MEA EDA 0 19 3 _ n Hex IPA n Hex EtOH MTBE EtOH n Hex CH CI 2 RN 80720WW 80720 V 98 2 wV 50 50 WW 3 99 1 50 50 v v 99 1 50 50 v v 60 40 100 0 v v 85 15 0 100 v v n Hex 1 0mL min 25 X 4 6mmx250mm 1 4 1
55. 7 1 5 0 5 m 7 1 6 HPLC 7 1 7 7 1 8 2 85 15 v
56. pH 2 0 pH2 0 HPLC pH2 0 pH2 0 A 50mM 3 40g KH PO FW 136 09 HPLC 500mL B 85wt HLPO A B pH 2 0 20mM pH9 0 A 20mM 0 79g NH HCO FW 79 06 HPLC 500mL A pH 9 0 100mM pH2 100mM A 100mM 9 20g KPF FW184 07 HPLC 500mL B 85wt HL PO gt A B pH 2 0 20mM pH9
57. DEA EDA p 6 1 2 2 Column CHIRALPAK IB 4 6mmX 250mm Flow rate 1 0mL min Temp 25 oo Propranolol 1 DEA 0 3 cs DEA 0 1 0 2 4 6 8 10 12 min 0 2 4 6 8 10 12 min n Hex IPA EDA 80 20 0 1 v v v i 0 EDA DEA n Hex n IPA 2 IC DEA p 6 1 2 2 Column CHIRALPAK IC 4 6mm Xx 250mm Flow rate 1 0mL min Temp 25 C DL Metanephnine MTBE MeOH Additive 94 6 0 1 v v v Column CHIRALPAK IC 4 6mm Xx 250mm CI Flow rate 1 0mL min 1 Team 25 Econazole MTBE MeOH Additive 98 2 0 1 v v v Column CHIRALPAK IC
58. 1 2 2 TFA DEA MEA EDA 0 1 2 4 wlemmlemeelmlwmlmlelmlm a 9 n 2 0 1 0 1 0 5 0 5 1 DEA MEA n BuA p 7 2 IB
59. 3 n Hex EtOH S0 2070 1 WWv MTBE EtOH 98 2 0 1 v v vy CH CL EtOH 80 20 v v COOH UH H oN I Oxprenolol OH Tropic acid Furoin a oc Fr WW Column CHIRALPAK IB Column CHIRALPAK IC Column CHIRALPAK IA 4 6mmX 250mm 4 6mm 250mm 4 6mmX 250mm Flow rate 1 0mL min Flow rate 1 0mL min Flow rate 1 0mL min Temp 25 Temp 25 Temp 25 n Hex n EtOH CHLCI MTBE t y Phenyl y butyrolactone Indapamide CI NT 0 O O NHz IF IE 0 5 10 1 20 25 30 0 4 8 12 Retention Time min Retention Time min Column size 4 6mml D X250mmL Column size 4 6mml D X250mmL Mobile phase n Hex EtOH 90 10 v v Mobile phase n Hex EtOH DEA 50 50 0 1 V V V Flow rate 1 0mL min Flow rate 1 0mL min Temperture 25 Temperture 25 Detection UV220nm Detection UV254nm 5 BenzyIhydantoin Cisapiride a CI Y 0 ME NH N NX FF 0 oO N O Oo F IF IF IE IE DD ID_ IB IA 0 5 10 15 20 25 30 0 8 12 1 20 Retention Time min Retention Time m
60. p 8 4 1 2 1 1 2 1 p 6 1 2 2 p 8 3 p 8 3 p 8 4 p 8 4
61. 10 100mM TT eo PE NaN 1 p 4 7 2 15 3 4 100mM 5 10mM 7 3 2 pH CHIRALPAK AGP pH 1 pH pH pH 5 4 hydroxyphenyl 5 phenylhydrantoin 4 037 AA 7 0 IPA 95 5 3 861 AA S 8 IPA 95 5 s AA 4 5 TPA 95 5 1 4 5 5 8 7 0
62. 10mM OA DMOA 2mM OA 5mM DMOA 7 2 4 0 20mg mL 5 10 ECT 0 5um 100
63. 23 2 2 2 24 2 2 3 25 2 3 5 2 3 1 25 2 3 2 26 2 3 3 26 2 4 27 2 1 2 1 1 CHIRALPAKY AD H CHIRALPAK AD 3 OD H nm 2 90 10 v v OD 3 n 2 90 10 v V CHIRALCELYOJ H CHIRALCELY OJ 3 Cellulose tris 4 methylbenzoate OJ H5um 0 33um 0J H n 2 90 10 v v 0J 3 n 2 90 10 v v CHIRALCELY OZ H CHIRALCELY OZ 3 Cellulose tris 3 chloro 4 methylphenylcarbamate OZ H 5um OZ 3 3um 0Z H n 2 90 10 VV OZ 3 n 2 90 10 VV CHIRALCELY OX H CHIRALCEL OX 3 LE Cellulose tris 4 chloro 3 methylIphenylcarbamate OX H5
64. CHIRALPAK AGP 5uUm 2 85 15 v v CHIRALPAKYCBH 5um 2 85 15 vW CHIRALPAKYHSA 5uUm 2 90 10 v v 7 1 2 CHIRALPAK AGP CBH HSA 2 0X50mm 3 0X50mm 4 0X50mm 10X100mm 2 0x 100mm 3 0X100mm 4 0X100mm 10X150mm X 2 0X150mm 3 0X150mm 4 0X150mm 0 2mL min 0 5mL min 0 9mL min 4 0mL min 10MPa 102 kgf cm pH pH4 0 7 0 0 15 0 100mM 10 20mM 0 10mM
65. 100 HH N s 1 ZWIX trans 2 aminocyclohexanesulfonic acid ACHSA gt 1 R 2 R 6 1 2 2 3 x 150 mm 4x 150 mm X 3 x 250 mm 4 x 250 mm 02 0 5mL min 02 30MPa 305 kgf cm2 5 lt 45 HPLC 6 1 3 CHIRALPAK ZWIX CHIRALPAK ZWIX zwitterionic CHIRALPAK ZWIX C
66. n 1 6 1 p 32 2 8 LC MS 7 DEA lt MM pH9 0 20mM RI 3 kN 2 mM 2 SS SA DEA
67. 1 1 2 59 2 2 o Column CHIRALPAKYAD H 0
68. OO OO OO p 6 1 2 2 p 6 2 p 8 3 CL p 8 4 1 p 10 1 3 1 1 3 2
69. UV 15 H VTAMIN 6 CHIRALPAK ZWIX CHIRALPAK ZWIX QUININE DERIVED 8S 9R QUININE DERIVED 8R 9S 8 SOS sO H H N 1 1 N gt 1 5 2 9 0 EO 17R 2 R Covalently bonded on 3um spherical silica gel CHIRALPAK ZWIX ZWIX trans 2 aminocyclohexhane sulfonic acid ACHSA chinchona alkaloid ZWIX ZWIX
70. pH PH pH pH 4 0 7 0 7 Mephenytoin O NH mAU 2 623 AA 7 0 1PA 98 2 3 274 5 AA 5 8 IPA 98 2 AA 4 5 IPA 98 2 2 561 3 176 AA pH pH 2 4 hydroxypheny 5 phenyIhydrantoin 18 AA 5 8 IPA 95 5 AA 4 5 IPA 95 5 pH Gi O H Hs Ketamine EZ 6 275 6 936 8 A AA 7 0 IPA 95 5 2818 AA S 8 IPA 95 5 10 5 5 o 5 5 5 o o 15 10 AA pH KU 7 3 3 CHIRALPAK AGP
71. O QA sm oO O 5 gt NH a 8 a CN H Go 5 Hydroxy DL Trp GO a 1 36 9 Oo Rs 4 18 6 2 3 ZWIX ZWIX trans 4 Hydroxy DL Proline CHIRALPAK ZWIX CHIRALPAK ZWIX 9 6 2 4 LC MS LC MS Homophenylalanine oo 2 Amino 2 phenyIbutyric acid 40Er05 a OH Wi 1 NH2 3OEsO5 1 NHz O do SES O 5E 5Erd5 1 OE S 1 5Ee05 15ErO5 1OEx05 OES EM SEA LE CE 9 4 5 10 9 1 3 3 4 5 time minl time min LC MS Q Trap MR
72. Amylose tris 3 5 dimethylphenylcarbamate OR D AD RH 5um AD RH 3um Amylose derivative H AD RH 60 40 v v NM AD 3R 60 40 v V CHIRALPAKY AS RH CHIRALPAKY AS 3R A H ol Amylose tris S a methylbenzylcarbamate OR 9 AS RH 5um AS 3R3 um Amylose derivative O AS RH 60 40 v v sinca 99 AS 3R 50 50 VV CHIRALPAKY AY RH CHIRALPAK AY 3R AU Amylose tris 5 chloro 2 methylphenylcarbamate OR 9 AY RH 5 um AY 3R 3um Amylose derivative AY RH 30 70 v v silica gel H CH AY 3R 30 70 v v CHIRALPAKY AZ RH CHIRALPAK AZ 3R on a Amylose tris 3 chloro 4 methylphenylcarbamate 6 AZ H5um AZ 3 3um Amylose derivative AZ RH 50 50 v v silica gel H AZ 3R 50 50 v v CHIRALCEL OD RH CHIRALCEL OD 3R NM ch
73. CoIUmn CHIRALPAKe A 4 6mm x 250mm RN Flow rate 1 0mL min Temp 25 Methaqualone n Hex IPA 80 20 v v In Hex MeOAc 80 20 v v n Hex Acetone 85 15 v v MTBE EtOH 80 20 v v K1 1 45 2 36 k1 1387 a 1 70 k1 1 42 a 1 33 20 0 RT Toluene n Hex THF 70 25 5 V V V ki 0 54 g 1 96 n Hex CHCI 50 50 V V n Hex CH CIL 75 25 v v n Hex THF 85 15 v v k1 0 64 g 1 79 k1 2 90 g 2 36 k1 3 14 g 1 63 n Hex nh IPA 2 MeOAc Acetone MTBE t EtOH CHC THFa 1 7 4 IB IB p anisoin Column CHIRALPAKeB 4 6mm 250mm O Flow rate 1 0mL min Temp 25 OH Dp Anisoin Mobile phase n Hex EtOH 75 25 v v Mobile phase n Hex IPA 70 30 v v Mobile phase n Hex THF 80 20 v v yl LF rin 1 i Fr 1 i k1 2 65 a 1 07 Rs 1 47 k1 4 54 a 1 13 Rs 2 60 k1 2 02 a 1 18 Rs 2 75 Mobile phase n Hex CH Cl 20 80 v v Mobile phase n Hex EtOAc 60 40 v
74. 60 40 VV p10 1 3 1 p10 1 3 2 gt pH9 0 pHZ7 0 25 1 6 2 pH2 0 HPLC
75. CROWNPAK CR I CROWNPAK CR I 7 QO Immobilized to Immobilized to silica gel silica gel CROWNPAK NH _ 51 E GE _ 5 13 _ 5 1 4 _ 5 1 5 6 16 45 _ 52 46 _ 5 2 1 1 46_ _ 5 2 2 pH _ 523 4 _ 5 2 4 _ 5 3 CROWNPAK CR _ 249 EA 4 249 SN ZAI S Q _ 53 4
76. Cellulose tris 3 5 dimethylphenylcarbamate Ro O OD RH 5um OD 3R 3um Cellulose derivative R OD RH 60 40 v v CI O CH R CH CI QO R h 3 1 2 CHIRALPAK AD RH 3R AS RH 3R AY RH 3R AZ RH 3R CHIRALCEL OD RH 3R OJ RH 3R OZ RH 3R OX RH 3R 14 HPLC 30MPa 305kgf cm2 pH7 0 pH pH2 0 9 0 i ii 25 Ee 5 40 pH7 5 25 pH7 3 1 3
77. v v v v 50 50 0 5 2 0 2 1 0 n 50 50 3 gt CROWNPAK CR I CR I 95 5 2
78. pH 9 0 CH CN HCO0OH NHHCO 1 7 8 Mobile phase HCOOHaq pH 2 0 CH CN 60 40 Flow rate 0 5mL min Temp 25 Detect UV254nm 5 30 HCOOHaq pH2 0 CH CN 7030 VW CH CN 1 7 9 8 52 9 37 SS 4 Phenyl 2 oxozolidinone Column CHIRALPAK IA Mobile phase HO CH CN 70730 4 8 12 16 20 0 4 8 12 16 20 0 4 8 12 16 Flow rate 0 5mL min D UV254 Temp 10C 25 G gt _ 420 a CH CN 2 CHIRALPAKYAD H CHIRALPAK AD 3 CHIRALPAKYAS H CHIRALPAKY AS 3 CHIRALPAK YAY H CHIRALPAKY AY 3 CHIRALPAK Y AZ H CHIRALPAKY AZ 3 CHIRALCELYOD H CHIRALCELY OD 3 CHIRALCELYOJ H CHIRALCELY OJ 3 CHIRALCELYOX H CHIRALCELY OX 3 CHIRALCELYOZ H CHIRALCELY OZ 3
79. 1 50 50 60 40 70 30 0 RI 1 CHIRALPAK AD RH 3 4 2 Et 2 Methyltetralone 2 Phenyl 2 butanol a 2 0 5 1 26 122 0 3 0 4 29 0 65 1 06 15 0 3 0 37 50 50 35 65
80. DEA EDA p 7 3 IC DEA MEA p 7 MEA EDA 29 Column CHIRALPAK IA 4 6mmX 250mm Flow rate 1 0mL min Temp 25 5 76 6 99 Flurbiprofen aes 0 10 20 30 40 50 60 0 4 8 12 16 20 n Hex IPA 90 10 v v n Hex IPA TFA 90 10 0 1 v v 16 10 Disopyramide NH gt A 0 10 20 30 40 50 60 0 5 10 15 20 25 30 n HexJIPA 90710 VV n HexIPDEA 90 1070 1 v Hex IPA 2 DEA TFA B
81. toluene 1 7 6 a 2 Column CHIRALPAK IA 4 6mmX 150mm Flow rate 0 5mL min Temp 25 HO THF 80 20 HO CH CN 70 30 HO IPA 65 35 HO EtOH 55 45 HO MeOH 40 60 9 7011 00 9 88 TU 11 16 10 3 co 11 78 12 86 9 65 0 10 35 4 Phenyl 2 oxazolidinone _ ma HO THF 65 35 HO CHCN 60 40 HO IPA 50 50 HO EtOH 50 50 HO MeOH 40 60 5 78 6 04 5 88 5 70 6 28 5 3 1 7 67 i NH 8 90 0 9 48 5 Methyl 5 phenylhydantoin THF CH CN IPA 2 EtOH MeOH 1 7 7 5 Methy 5 phenyIhydantoin Flurbiprofen Perisoxal CHIRALPAK IA 7 OY s PT CH CN 60 40 CH CN 70 30 CH CN 30770 0 5 mLmin 1 0 mUmin 1 0 mLmin HCOOHadq pH 2 0 NH HCO aq
82. 0 1mL min En C wi n Hex EtOH TFA H O 50 50 0 5 2 259C 0 4mL min EEtOH TFA CH CN HCIO HCOOH 5 2 2 pH CROWNPAK pH HCIO aq CH CN 80 20 v v COOH ST 02mL min 200nm 25C NH Cysteine a 4 70 Rs 10 18 a 4 16 Rs 5 64 0 5 10 pH1 0 pH1 5 pH2 0 5 2 3 TFA UV NH HO 2 Tyrosine a 2 06 Rs 3 23 HNO uv240nm min 5 2 4 CH CN THF Acetone MeOH EtOH IPA CH CN 2 HCIO aq pH1 5 Modifier 0 2mL min 200nm 25 Tyrosine CH CN 20 T
83. pH 1 5 CH CN 80 20 CH CN MeOH EtOH IPA 2 THF AT pH 1 0 2 0 pH7 0 pH pH UV THF 2
84. pH pH2 0 70 3 pH k pH2 0 70 7 00 3 00 pH EE K OO Kk 3 00 pH pH LD 0 LL 5 fi 1 CHIRALPAK AD RH 50mM 60 40 v v 0 5ml min 25 UV 254nm 3 pH 3 4 5 pH
85. 14F TEL 03 6711 8222 FAX 03 6711 8228 530 0011 3 B TEL 06 7639 7221 FAX 06 7639 7228 http www daicelchiral Com E mailchiral jp daicel com E mail chiral chiraltech com E mail cte chiral fr l E mail chiral ctc daicel com E mail chiral chiral daicel com 201503AP3K
86. 4 6 mm x 250 mm Flow rate 1 0mL min ET EE WE ET a 4 Temp 25C ss 15 7 CH CL n Hex 80 20 v v OH Rs 18 2 a CH CL 100 CO OH 1 5 Dihydroxy 1 2 3 4 tetrahydronaphthalene Column CHIRALPAK IC 4 6 mmX 250 mm Flow rate 1 0mL min Temp 25 CH CN EtOAc n Hex n MeOH 1 UV RI ELSD UV 6 UV UV nm UV nm TH 412 lt 190 MBE 2 233 14 245 256 DMF 268 DMAc 268 2 DMSO 286 210 284 gt 205 2 330
87. Vali ZWIX A ELSD 4 3 L D 2 SM THF 6 3 2 sy gt O2N NBD F H O Column CHIRALPAK ZWIX 4 0X250mm Mobile phase MeOH CH CN H 0 49 49 2 v v v 50mM FA 25mM DEA Flow rate 0 40 mL min Temperature 25 C OH Detection UV470nm OzN 6 0 10 20 30 OH NZ N a H 0 N O min 2 0 N 1 2 NBD Alanine ON OH OH NZ7 D H oO 0 N 3 6 NBD Serine NBD F 4 7 2 1 3 5 NBD Aspartic acid 6 3 3 2 CHIRALPAK ZWIX 3 250 mm 0 50 mL min 25 ELSD O QO D oe TI NH Ng NH DL 2 Amino DL Norleucine DL 2 Amino Caprylic acid butyric acid 0 2 4 6 8 10 12 14 min 0 2 4 6 8 10 12 min 0 2 4 6 8 10 12 14 min L O O
88. 1 _ 54 2 1 _ 543 5 1 5 1 1 CROWNPAKY CR I 1 18 crown 6 ether 5 um J 95 5 v v CROWNPAK CR I SS R 18 crown 6 ether OW 5 um 95 5 v v CO immobilized to silica gel 5 1 2 X 3 0X150mm 30MPa 305 kgf cm2 a pH pH 1 0 7 0 5 40 HPLC
89. 2 MTBE 12 2 2 1 2 2 1 p 24 2 2 2 p 24 12 P 24 12
90. 2 1 6 HPLC ET RD TR 1 HH PLC 2 3 1 7 1 HPLC 0 5mL min 2
91. 25 75 3 4 3 2 5 25 40 5 40C k pH7 0 25 C CHIRATLPAR AD RH 0 40 Y w 0 5mL min UV 5dnm methyL1 tetralone UV 220mm 2phenwL2 butanol 2 3 4 4
92. 8 W 8 8 1 7 3 6 PH 10 mM AA 7 0 IPA 95 5 5 649 4 DMOA N N Dimethyloctyl amine Atropine HFBA Heptafluorobutyric acid J OA Octanoicacid ART 0 IPA 95 5 SmM HFBA Fenoprofen J AA C7 0 IPA 95 5 2mM OA en ln Et AA 7 0 EtOH 95 5 3 869 4 418 s 3 107 AA 7 0 IPA 98 2 2mM OA AA 7 0 EtOH 95 5 SmM DMOA IN IS leH co gt 10 103 1 we AA PN The pes7 Solution for You CPI 108 8230 2 18 1 JR
93. Flurbiprofen 0 0 F 6 0 4 0 0 n HexIPA 90 1 0 VV n Hex IPA AcOH 90 10 0 1 VvV Disopyramide 1 0 n Hex IPA 90 10 V V V n Hex IPA DEA 90 10 0 1 VvV nh Hex nh IPA 2 AcOH DEA 2 2 3 TFA DEA MEA EDA 0 1 12 _ n Hex IPA n Hex EtOH CH CN MeOH 80 20 vV 80 20 VV 100 0 v v 100 0 WV 2 5060 70 99 1 50 50 VV 80 20 100 0 v v 0 100 10070 WV EtOHLIPA n Hex 1 0mL min 25 X
94. 4 6mmX250mm n Hex n EtOH CH CN MeOH IPA 2 2 3 1 NIC Column CHIRALPAK AD F 4 6mmxX 250mm Temp 40 Flow rate 1 0mL min Flurbiprofen 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 0 5 10 15 20 25 30 35 40 45 50 55 60 Minutes Minutes n Hex IPA AcOH 90 1070 1 VV V n Hex IPA AcOH 100 170 1 VV V nh Hex nh IPA 2 AcOH 26 2 3 2
95. 3X150mm 0 4 0 5 mlmin 4X150mm 0 8 1 0 mmin 25 1L MeOH 490mL CH CN 490mL 20mL 1 9mL 2 6mL 1 Kk 2 Kk gt 8 MeOH MeOH H 0 98 2 100mM 50mM DEA HO 20 MeOH CH CN9 or THF 60 80 2 3mm 0 2mL min 4mm 0 4mL min 3X250mm or 4X250mm 1 LC MS MeOH H O 98 2 0 25mM Yes 1 Uy 0 5mm s ZWIX gt ZWIX or ZWIX ZWIX 6 2 2 CH CN MeOH lt MeOH lt MeOH H O CM CM i
96. AZ H AD 3 AS 3 AY 3 AZ 3 CHIRALCEL OD H OJ H OZ H OX 3R OD 3 OJ 3 OZ 3 OX 3R 3 ODS J E 3 1 29 3 1 1 9 3 1 2 30 3 1 3 30 3 1 4 30 3 1 5 30 3 1 6 30 3 1 7 30 3 1 8 30 3 2 31 3 2 1 2 3 3 32 3 3 1 22 3 3 2 34 3 4 35 3 4 1 BS 3 4 2 8 3 4 3 36 3 4 4 pH 36 3 4 5 pH
97. GO_ _ 32 1 31 7 23 61 3 3 32 7 2 4 61 3 3 1 32 7 2 5 61 3 3 2 34 _ 73 CHIRALPAKYAGP 62 _ _ 3 4 35 _ 7 3 1 62 _ _ 3 4 1 35 _ 73 2 tpH 6 63 _ 3 42 35 7 3 3 64 3 4 3 36 7 3 4 64 3 4 4 pH 36 73 5 65 3 4 5 pH 37 _ 7 3 6 65 3 4 6 37 1 1 CHIRALPAK TA CHIRALPAKSIA 3 CHIRALPAK TB CHIRALPAK1B 3 CHIRALPAK IC CHIRALPAKSIC 3 CHIRALPAK TD CHIRALPAKSID 3 CHIRALPAK TE CHIRALPAKIE 3 CHIRALPAK IF CHIRALPAKIF 3 CHIRALPAK AD H CHIRALPAK AD 3 CHIRALPAK AS H CHIRALPAK AS 3 CHIRALPAK AY H CHIRALPAK AY 3 CHIRALPAK AZ H CHIRALPAK AZ 3 CHIRALCEL OD H CHIRALCEL OD 3 CHI
98. 4 6mm Xx 250mm ee Flow rate 1 0mL min 7 19 Temp 25 Flavanone yy 14 69 0 4 8 12 16 0 4 8 12 16 20 n Hex IPA 90 10 n Hex EtOH 90 10 nh Hex nh IPA 2 EtOH 2 4 nh 2 90 10 vv 3 CHIRALPAKYAD RH CHIRALPAKY AD 3R CHIRALPAKYAS RH CHIRALPAKY AS 3R CHIRALPAKYAY RH CHIRALPAKY AY 3R CHIRALPAKYAZ RH CHIRALPAKY AZ 3R CHIRALCEL OD RH CHIRALCEL OD 3R CHIRALCEL OJ RH CHIRALCEL OJ 3R CHIRALCEL OX RH CHIRALCEL OX 3R CHIRALCEL OZ RH CHIRALCEL OZ 3R CHIRALPAK AD RH AS RH AY RH AZ RH AD 3R AS 3R AY 3R AZ RH CHIRALCEL OD RH OJ RH OZ RH OX RH OD 3R 0J 3R OZ 3R OX 3R CHIRALPAK AD H AS H AY H
99. pH 2 0 pH2 0 HPLC pH2 0 pH2 0 A 50mM 3 40g KH PO FW 136 09 HPLC 500mL B 85wt HLPO gt A B pH 2 0 20mM pH9 0 A 20mM 0 79g NH HCO FW 79 06 HPLC 500mL A pH 9 0 100mM pH2 0 100mM A 100mM 9 20g KPF_ FW184 07 HPLC 500mL B 85wt HPO A B pH 2 0 20mM pH9 0 A
100. v v CHIRALPAKS IC CHIRALPAK IC 3 Cellulose tris 3 5 dichlorophenylcarbamate lOSe derivali ra N CI C5um IC 33um IC IC 3 n 2 90 10 v v CHIRALPAK ID CHIRALPAK ID 3 Amylose tris 3 chlorophenylcarbamate ID5um ID 33um ID ID 3 n 2 90 10 v v Immobilized to silica gel OR O RO OR O n Amylose derivative immobilized to silica gel CHIRALPAKY IE CHIRALPAK IE 3 A DL 2 O Amylose tris 3 5 dichlorophenylcarbamate YIOSe derivativgg B CI IE5um IE 33um HH IE IE 3 n 2 90 10 v v CHIRALPAK IF CHIRALPAK IF 3 A BE O Amylose tris 3 Chloro 4 methylphenylcarbamate Amylose derivative RB H IF 5um IF 3 3um IF IF 3 n 2 90 10 v v 1 1 2 immobilized to silica gel
101. 0 A 20mM 1 24gH BO FW61 83 HPLC 1L B 20mM 3 81gNa B 0 10H O FW381 37 HPLC 500mL B A pH9 0 3 4 p32 3 3 1 A B 1 2 0 3 4 1 2 5C 25 40
102. 3 1 56 _ 223 25 _ 63 2 16166 56 _ 2 3 25 _ 63 4 2 57 _ 233 1 25 _ 63 5 57 _ 2 3 2 26 6 3 6 57 2 3 3 26 _ 24 27 cr 7 1 59 7 1 1 59 3 1 29 7 1 2 59 3 1 1 29 _ 7 13 59 _ 3 1 2 30 _ 714 _ 3 1 3 30 _ 7 15 6 6 61 6 6 t 60 _ 3 1 4 30 7 16 60 3 1 5 30 7 1 7 60 3 1 6 30 7 1 8 60 3 1 7 30 _ 7 2 60 _ _ 3 1 8 30 _ 7 2 1 60 _ 3 2 31 _ 7 222
103. 5 1 2 23 1 3 1 10 5 1 3 43 1 3 2 10 5 1 4 44 1 3 3 1 5 1 5 45 1 4 12 _ 5 2 246 1 5 13 _ 5 2 1 346 1 5 1 13 _ 5 2 2 pH 46 1 5 2 13 5 2 3 47 1 6 14 5 2 4 47 1 6 1 14 5 2 5 48 1 6 2 15 _ 5 26 48 17 16 _ 5 3 CROWNPAK CR 249 1 7 1 16 _ 5 3 1 B 49 1 7 2 100 16 5 gt 3 2 49 1 7 3 IA 17 5 3 3 50 1 7 4 IB 17 5 3 4 50 1 7 5 18 _ 54 CRPWNPAKICR 5 1 7 6
104. CHIRALPAK IA IA 3 IB IB 3 IC IC 3 ID ID 3 IE IE 3 IF IF 3 1 29lc 2 0UUE22alg 4 6mm 30MPa 305kgf cm2 0 1 0 2mL min 0 5 1 0mL min 0 40 5 40 pH7 5 25C pH7 HPLC 1 1 3 n 2
105. FY 3 AA 7 0 IPA 95 5 6 AA 4 5 IPA 95 5 ul F 1 AA 7 0 EtOH 95 5 AA 4 5 EtOH 9575 4 794 5 222 1785 5 181 AA 4 5 CH CN 95 5 AA 7 0 CH CN 95 5 ros Iin AA 7 0 MeOH 95 5 AA 4 5 MeOH 95 5 1 2 k 15 ER 7 3 5 pH 100 mM 9 2 2 4 dichlorophenoxy propionic acid gt CI O 10mM AA S 8 IPA 95 5 Naproxen te LO 10mM AA S 8 IPA 955 co wn 358 MH Nr 2 842 3 807 2 903 75mM AA 5 8 IPA 95 5 75mM AA S 8 IPA 955 N 3 5 DNB DL leucine 10mM AA 4 5 IPA 9575 1 75mM AA 4 5 IPA 95 5 AA 7 583 4 191
106. v Mobile phase MTBE MeOH 98 2 v v EE 1 mn WI k1 2 39 a 1 19 Rs 1 47 kt 0 a 1 0 k1 1 11 a 2 16 Rs 10 67 n Hex n EtOH IPA 2 THF CH CL EtOAc MTBE t MeOH 1 7 5 Mobile phase n Hex CH Cl DEA Mobile phase CH CN EtOAc 50 50 0 1 v v v 70 30 v v 4 0 1 4 3 O N N 1 Bupivacain Methaqualone Rs 5 7 Rs 3 2 Column CHIRALPAK IA Column CHIRALPAK IA 4 6mm x 250mm 4 6mm x 250mm Flow rate 1 0mL min Flow rate 1 0mL min Temp 25 C Temp 25 C Mobile phase n Hex Toluene EDA Mobile phase n Hex THF Mobile phase n Hex THF MEA 80 20 0 1 v v v 60 40 v v 60 40 0 1 v v v 3 7 oO CH 3 9 oH 4 3 TO 4 8 be oe CH a Oxprenolol Mephobarbital Laudanosine Rs 6 0 Rs 7 7 Column CHIRALPAK IB Column CHIRALPAK IB Column CHIRALPAK IB 4 6mmX 250mm 4 6mmX 250mm 4 6mmX 250mm Flow rate 1 0mL min Flow rate 1 0mL min Flow rate 1 0mL min Temp 25 Temp 25 Temp 25 EtOAc
107. 20mM 1 24gH BO FW61 83 HPLC 1L B 20mM 3 81gNa B 0 10H O FW381 37 HPLC 500mL B A pH9 0 1 1 1 7 1 7 1 400 100 o N O 1 Glutethimide 400 300 200 100 4 0 2 BB 6 3 10 mn Retention me Column CHIRALPAK IA 4 6mm x 250mm Flow rate 1 0mL min Temp 25 C Detect UV274nm 100 0 1 V V YT 2 Phenoxypropionic acid Column CHIRALPAK IB 4 6mmx 250mm Flow rate 1 0mL min Temp 25 Detect UV274nm 1 7 2 100 100 N a N Praziquantel Retertion te Column CHIRALPAK IC 4 6mm x 250mm Flow rate 1 0mL min Temp 25 Detect ELSD 100
108. 50 V V 20 100 6 2 6 2 1 proton activity CHIRALPAK ZWIX CHIRALPAK ZWIX 20vol
109. DAICEL CHIRALPAK CHIRALCEL CROWNPAK CPI 1 1 3 _ 4 1 39 _ 1 1 1 3 4 2 39 1 1 2 3 4 3 40 1 1 3 4 4 4 40 1 1 4 4 _ 45 2420 1 1 5 4 _ 46 41 4 _ 47 41 1 1 7 4 121 NT TT TN 1 2 2 6 5 1 243 1 2 3 8 _ 5 1 1 uo 1 3 10 _
110. HF 20 Acetone 20 Q 3 16 Q 1 99 Q 2 82 Rs 9 67 Rs 6 06 Rs 6 55 Do UE UES Do UU 0 3 10 15 0 5 _ 10 15 0 5 10 15 min min min MeOH 20 EtOH 20 IPA 20 Q 2 61 a 2 86 a 3 00 Rs 4 47 Rs 5 40 Rs 5 68 d H VTAMIN 5 2 5 HCIO aq pH1 0 CH CN 80 20 VV HN COOH TT 0 2mL min 200nm QO NH Asparagine Rs 5 3 Rs 2 6 Rs 1 5 0 5 10 0 5 10 0 5 10 min min min 0C 15C 25C 5 2 6 CR I CR I wo QO N NH H N OH Flow rate 0 2mL min 3 H Tryptophan erythro 2 amino 1 2 diphenylethanol D L 0 2 4 6 8 0 2 4 6 8 min min D 0 2 4 6 8 0 2 4 6 8 min min Mobile phase HCIO aq pH1 5 CH CN 50 50 v v Mobile phase HCIO aq pH1 5 CH CN 50 50 v v Detection UV200nm Temperature 25 C Detection UV200nm Temperature 25 5 3 CROWNPAK CR 5 3 1 a 8 Y Column CROWNPAKY CR I 3X150mm COOH NH Pf COOH
111. HIRALPAK ZWIX MS UV CHIRALPAK ZWIX CHIRALPAK ZWIX 2 HPLC 6 1 4 20 30 40mL 100 100 50
112. M Mode CHIRALPAK ZWIX 3X150mmi d Mobile phase 25mMFA 12 5mM ammonium formate in MeOH CH CN H 0 49 49 2 v v v Flow rate 0 5mL min Temperature 40 6 3 CHIRALPAK ZWIX 6 3 1 Rs 2 7 L D 1 3 0X150mm 2 4 0 X250mm DL Amino acid MD Alanine Q Arginine B 1 9 D L Asparagine C 4 3 L D A MeOH CH CN Hz0 49 49 2 v v v Aspartic acid B x 0 5 UMM EA SOM DR B MeOH H20O 98 2 v v D 2 D L 0 2 5 50mM FA 25mM DEA Glutamic acid B 1 3 D L C MeOH CH CN 50 50 v v Glutamine D QO 3 2 L D 50mM FA 25mM DEA Histidine B 9 25 L D D MeOH THF HO 49 49 2 v v v lsoleucine A Q 4 6 L D 0mMFA 25mM DEA Leucine A 3 6 L D 0 5mL min 25 Lysine B 1 8 L D Methionine A 2 8 L D Phenylalanine A UV254nm 2 6 L D Proline A ELSD QO 10 0 L D X Serine D ELSD 1 0 Tryptophan B UV254nm D L MeOH Tyrosine A UV270nm QO 2 9 L D CH CN Threonine A ELSD 4 0 L D FA
113. Phenylalanine B Phenylalanine 0 5 10 0 2 4 6 8 min mim Mobile phase HCIO aq pH1 5 CH CN 80 20 v v Mobile phase n Hex EtOH TFA H O 50 50 0 5 2 v v v v Detection UV200nm Temperature 25 Flow rate 0 2 mL min Detection UV254nm Temperature 25 Flow rate 0 4 mL min NH COOH C Baclofene 0 2 CD B 8 10 Mobile phase HCIO aq pH1 5 CH CN 50 50 v v Detection UV200nm Temperature 25 Flow rate 0 2 mL min 5 3 2 1 CH CN THF Acetone MeOH EtOH IPA CH CN Column CROWNPAKY CR I 3X150mm a Amino E caprolactam Flow rate 0 2 mL min O NH HN NH Phenylethylamine 0 2 4 3 8 0 2 2 NM 6 8 10 min Mobile phase HCIOaq pH1 5 CH CN 80 20 v v Mobile phase HCIO aq pH1 5 CH CN 50 50 v v Detection UV200nm Temperature 25 Detection UV200nm Temperature 25 2 Amino 2 phenylethanol 0 2 Dhenylethano Mobile phase HCIO aq pH1 5 CH CN 80 20 WW H N OH Detection UV200nm Temperature 25 0 2 4 min 6 8 10 d H VMIN 5 3 3 O H HJN N COOH N YT H Leu Gly Gly OH 0 1 2 5 min Mobile phase HCIO aq pH1 0 CH CN 80 20 v v Detection UV200nm Temperatu
114. RALCEL OJ H CHIRALCEL OJ 3 CHIRALCEL OX H CHIRALCEL OX 3 CHIRALCELYOZ H CHIRALCELY OZ 3 _ gt 2 5 aii mn CHIRALPAK AD RH CHIRALPAK AD 3R CHIRALPAKYAS RH CHIRALPAK AS 3R CHIRALPAK AY RH CHIRALPAK AY 3R CHIRALPAKYAZ RH CHIRALPAK AZ 3R CHIRALCEL OD RH CHIRALCEL OD 3R CHIRALCEL OJ RH CHIRALCEL OJ 3R CHIRALCELYOX RH CHIRALCELY OX 3R CHIRALCELYOZ RH CHIRALCELY OZ 3R op K CROWNPAKY CR I CROWNPAKY CR I CROWNPAKY CR CROWNPAK CR 2W4 CHIRALPAK ZWIX CHIRALPAK ZWIX CHIRALPAK AGP CHIRALPAK CBH CHIRALPAK HSA HV JI NN UN MAI7 W 1 CHIRALPAK IA CHIRALPAK IA 3 CHIRALPAK IB CHIRALPAK IB 3 CHIRALPAK IC CHIRALPAK IC 3 CHIRALPAK ID CHIRALPAK ID 3 CHIRALPAK IE CHIRALPAK IE 3 CHIRALPAK IF CHIRALPAK IF 3
115. a D N OH NH B D H DL Pro DL Pipecolic acid Nipecotic acid 0 2 4 6 8 10 min 6 3 4 CHIRALPAK ZWIX 3 250 mm 0 50 mL min 25 ELSD O O QO A NH O 2N DL Leu DL Tyr DL Leu Gly Gly 6 3 5 CHIRALPAK ZWIX 3 X250 mm 0 50 mL min 25 ELSD NO NO COOH OH O HN COOH 1 O NH O NO 1 2 NH 1 NH 2 S 0 J CH oH Oo OH NN 2 Amino 3 phosphono DL Amethopterin propionic acid DNP DL Methionine sulfone DNP DL Norleucine OH 9 NH HO O NHz O OH MeO OH Mu OH NH O NH O NH 3 Hydroxy kynurenine Kynurenine 2 Methyl 3 3 4 dihydroxy 3 Methoxy DL tyrosine Phentl DL ananine O O OH O O O NH OH N NH OH HN OH i NH NH NH 1 Methyl DL tryptophan 3 1 Naphthyl DL alanine DLoQ Neopentylglycine DL Omithine Q Phenylglycine CHIRALPAKY AGP CHIRALPAK CBH CHIRALPAKY HSA
116. in Column size 4 6mml D X250mmL Column size 4 6mml D X250mmL Mobile phase n Hex IPA 80 20 VV Mobile phase n Hex IPA DEA 50 50 0 1 V V V Flow rate 1 0mL min Flow rate 1 0mL min Temperture 25 Temperture 25 Detection UV220nm Detection UV254nm Cetirizine Methyclothiazide O O CI El LTT OS 1 A IF 0 5 10 15 20 25 30 Retention Time min Column size 4 6mml D X250mmL Mobile phase n Hex EtOH AcOH DEA 50 50 0 1 0 1 v v v v Flow rate 1 0mL min Temperture 25 C Detection UV230nm n Hex nh EtOH DEA 20 8 12 16 Retention Time min Column size 4 6mml D X250mmL Mobile phase n Hex EtOH DEA 50 50 0 1 V V V Flow rate 1 0mL min Temperture 25 C Detection UV230nm IPA 2 AcOH 1 1 3 1 3 1
117. re 25 C Flow rate 0 4mL min O N CCOOH H H Ala Phe OH 0 10 15 20 25 30 Mobile phase HCIO aq pH1 5 CH CN 80 20 v v Detection UV200nm Temperature 25 Flow rate 0 4mL min 5 3 4 Column CROWNPAKY CR I 3X150mm H Leu Phe OH O HN COOH 0 10 20 mn 30 40 50 Mobile phase HCIO aq pH1 0 CH CN 40 60 v v Detection UV200nm Temperature 25 Flow rate 0 2mL min COOH HN S NH COOH Cystathionine 0 5 0 15 20 min Mobile phase HCIO aq pH1 0 CH CN 90 10 v v Detection UV200nm Temperature 25 Flow rate 0 2mL min CR I CR I 0 ulli Mobile phase n Hex EtOH TFA H O 50 50 0 5 2 v v v v Detection UV200nm Temperature 25 Tyrosine NH HO 2 Column CROWNPAK CR I 3 X150mm Flow rate 0 4mL min SS N NH Histidine Mobile phase n Hex EtOH TFA H 0 50 50 0 5 2 v v v v Detection UV200nm Temperature 25 B 10 Mobile phase n Hex EtOH TFA H 0 50 50 0 5 2 v v v v Detection UV254nm Temperature 25 5 4 CROWNPAK CR CROWNPAK CR CROWNPAKe CR
118. um OX 33um OX H n 2 90 10 v v OX 3 n 2 90 10 VV Cellulose derivative silica gel Cellulose derivative Silica gel OR A O CH Amylose tris 3 5 dimethylphenylcarbamate PIN 2 lt N AD H 5 um AD 33um Amylose derivative H AD H n 2 90 10 v v CH AD 3 n 2 90 10 v v CHIRALPAKY AS H CHIRALPAK AS 3 AU RC Amylose tris S a methyIbenzylcarbamate AS H5um AS 33um Amylose derivative O AS H n 2 90 10 v v BIICG OO AS 3 mn 2 90 10 v v CHIRALPAK AY H CHIRALPAK AY 3 A Amylose tris 5 chloro 2 methylphenylcarbamate OR 0 W AY H 5 m AY 3 3um Amylose derivative M a AY H n 2 90 10 v v silica gel H CH AY 3 n 2 90 10 v V CHIRALPAKY AZ H CHIRALPAKY AZ 3 on
119. v HPLC 1 HPLC HPLC 0 1mL min 1 0 5mL min 0 5mL min 2 0 8 0 9mL min 10 4mm 2mm 3mm 2 3 1 3 HPLC
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