The ChemicalTimes 通巻183号
Contents
1. 2 9 COO S032 32. 1991 1996 BINAP
3. 2 1966 1980 BINAP
4. MBL 28 4 56 26 13 17 2 18 2 27 3 2 2 31 23 6 5 RNA
5. SPring 8 BERI 1 JAPAN 6 3 4
6. NORIO SUZUKI SHIZUOKA AGRICULTURAL EXPERIMENT STATION 15 C 1 1 RQ RG 2 SQ NOVA 30
7. OH OH O O H OH Xx ee S X OH H 1 3 2 N e1 O 10
8. sugar nucleotide Glc Gal N GlcNAc 1 5 1 C1 0H
9. 2 Morris 5 No 1 2002
10. 3 No 1 2002 THE CHEAICAL TIMES 1 2001
11. 5 1 a Ohkuma T Ooka H Hashiguchi S Ikariya T Noyori R 7 Am Chem Soc 1995 117 2675 2676 hb Ohkuma T Ooka H Ikariya T Noyori R 7 Am Chem Soc 1995 117 10417 10418 c Ohkuma T Yamakawa M Ikariya T Noyori R J Org Chem 1996 61 4872 4873 d Ohkuma T Ikehira H Ikariya T Noyori R Synlett 1997 467 468 e Ohkuma T Doucet H Pham T Mikami K Korenaga T Terada M Noyori R 7 Am Chem Soc 1998 120 1086 1087 f Doucet H Ohkuma Murata K Yokozawa T Kozawa M Katayama E England A F Ikariya T Noyori R Angew Chem Int Ed Engl 1998 3Z 1703 1707 g Ohkuma T Doucet H Pham T Mikami K Korenaga T Terada M Noyori R J Am Chem Soc 1998 495 1086 1087 h Ohkuma T Koizumi M Doucet H Pham T Kozawa M Murata K Katayama E Yokozawa T Ikariya T Noyori R Am Chem Soc 1998 120 13529 13530 G Noyori R Ohkuma T Pure Appl Chem 1999 71 1493 1501 5 Ohkuma T Koizumi
12. 7 1 TAPAN 2 3
13. 8 No 1 2002
14. 6 1 2 2 JAPAN 2 6 2 JAPAN 6
15. THE HEAAICAL TIAAES oH OH 9H ss O i 2 CJ STx gt 9996 yleld 97 ee gt 99 yleld 98 ee X S 95 yieid 99 ee S02 95 yleid 98 ee OH IH OR LN gt 97 yield 95 ee A CH CHa 2 n 0 94 yield 75 ee R C2Hs n 1 94 yieid 93 ee R C2Hg n 3 99 yeld 95 ee 68 yleld 92 ee OzCHs QO Ci 3 Ch CaH RuCIS S Tsdpenl cymene HCOOHN C2Hss HpMF 4 No 1 2002 carbonic anhydrase inhibitor MK 0417 2 95 ee
16. CHazoHOH CHzCO ms NN ME CML RT N RR ACOR 16 electron amide oonPIX 18 elechon hydride complex Ts pCHsCaH4SOz coordinativeiy saturated ts Ts R ey 3 N AN 0 ow catatyat precursor 2 THE CHEMICAL TIMES 2
17. BINAP 2 DME P 1 14 3 6 2
18. DNA NK4 ABC HTS
19. Man U UDP Gal UDP Man Fuc G GDP Fuc Comparative Biochemistry of Milk Oligosaccharides VHD Characteristcs on the Chemical Structure and Their Application No 1 2002 5 N NeuAc CMP NeuAc ADP GDP UDP dTDP
20. RQ RQ r 0 993 9 0 974 9 0 803 5 mg 5 80 100 5 30 50 80 100 12 3 200 400 60 70 4 a 14 16 1 3 5 5 10
21. 7 dtueat cove en 7 AR Goo AR 7 28 93 992 yed SC 200 1000 chiral Hu cat RuCi S S Tsdpenl mesityene a OT 96 ee A mCl 97 ee 97 ee pC 95 ee moOCHs 98 ee POCH3 97 ee R Gs 99 ee 70 yield 83 ee CHg 99 ee 6 11 3 97 ee
22. 1 1 2 100 1 2 2 2 400 000 3 4 5 1
23. AH THE CHEAICAL TIMES No 1 2002 SNP 6 8 3
24. 1 5 100m 120m 1 RQ 1 5 RQ 6 320ppm No 1 2002 3 RQ 1 2 3 200 R2 0 884 29 y 0 735 0 428x 50 3 100 50 0 190 200 300 RQ mg 100g 3 RQ 400 2 P 5 10 20 30 40 50mg 4
25. 1 2 1 2 6 2000 4 o Ce og Cts 6H oH SC 1000 time h yeld ee yleld drmeso ee 025 96 0 24 lt 1 0 4 4 chirat Ru cat 0 005 mmol HCOOHN CzHsjs 3 172 6 0 95 Min DMF OH OH k H cat ts Lat ts cat pts OH OH OH jnv AgKs 56 OH OH co Cg cm CeHe OH OH OH 4 4
26. RQ 2 10 2 RQ 2 1 CSX 16 No 1 2002 THE CHEAICAL TIAES 3 10 mg e 4 3500 5000 5 6 900 1800 6 500 1500 3500 5000 4 1 1700 2600 2 1300 2200 4 900 1800 1 2 4000 5000 3 4 1800 3600 5 6 500 1500
27. 6 5 BA 1 2 THE CHEAICAL TIMES No 1 2002
28. HA 3 N a1 Gal 81 4 GlcNAc e1 POs 2 HA 1 GlcNAc e1 HexNAc o1 4 2 3 20 6 N g1 Neu5Ac e2 6 Gal 21 4 GlcNAc el1 POs 6 N 6 Neu5Ac e2 6 Gal 81 4 GlcNAc 6 POs GlcNAc 3
29. 2 Utilization of Mobile analyser in the Agricultural field Diagnosis of plant and soil by handy reflactometer RQ flex Part 1 THE CHEMICAL TIMES No 1 2002 a 50 8 21 2 200ppm RQ 9 7 100 4 RQ 1 1 START 1 60 RQ 7 N 8 21 2 50 Y 0 56X 51 0 742 30 9
30. 6 7 a 6 6 BA 5 G G 1 33 LE 9 61 EE tGLE Ne RIT 9 01 WE AE AL O 0 6 4 EAIO 9 2 Y GQ 44 4 M32 TG VRE 13
31. GDP 21 EL
32. 3 0 195 TADAO SAITO Dr Agric Laboratory of Animal Products Chemistry Graduate School of Agricultural Science TOHOKU University TADAS URASHIMA Dr Agric Department of Bioresource Chemistry OBIHIRO University of Agriculture and Veterinary Medicine 20 2 3
33. BA BA 1 2 6 4 6 4 1 BA 5 6 4 2 SPring 8
34. Com 6 3 6 3 1 6 3 2
35. HA 3 UDP UDP GlcNAc 5 510 ppm 2 1P 1 ong range 22 No 1 2002 GlcNAc c 1 PO4 TH NMR 5 382ppm HA 3 1 a 2 HA 3 HSQC 4 HA 3 N 1 e
36. l c 10 1 2 100 5 225mg 2 E 15000 14000 R2 072 9 13000 y 1 99e 004 846x 12000 11000 9 10 1f 12 13 14 15 1 mm 2 1
37. JAPAN 6 2 1 TSUNEAKI SAKATA Ph D Shionogi Research Laboratories Shionogi amp Co 10 2 500 5 100 10 1
38. 2 28 3 6 2 2 56 9 15 11 56 4 12 4 14 15 1 13 12 26 7 13 3 6 2 3
39. KUNIHIKO MURATA Central Research Laboratory Kanto Chemical Co Imc TAKAO IKARIYA Graduate School of Science and Engineering Tokyo Institute of Technology mle 2 BINAP 3 3 2
40. No 1 2002 gH 6 2 98 yleld 82 ee Rucat ReCk xyfblnapi S 1 2 cyclohexanediarmlne KO Bu 1 R 60 BMS 181000 i Ay Denopaming AY Fuoxetine N NT i i 0 BMS 181100 2 NH
41. 4 E O DE 9 PT 1 1 1 2 7 9 4 EAE ER Ti I 6 Y CE 01 PTET 0 4 4 lt f1 7 2 1 21 2 Y 4 y 1 2 Z 4 MSY Y 1 7 3 ED EDT 7
42. 20 3 N e1 Neu5Ac g2 3 Gal 81 4 GIcNAc al PO3 6 N et 3 Neu5Ac a2 3 Gal g1 3 GalNAc g1 POs 3 2 Neu5Ac g2 3 Galal1 PO3 4 1 Neu5Ac g2 3 Gal 81 3 Neu5Ac e2 6 GlcNAc c1 POs3 N Fuc e1 2 Gal 1 9 Fuc o1 3 1GlcNAc el POs N THE CHEAICAL TIMES No 1 2002 GalZ21 4GlcNAc 1 Thke Ckemical Times No 154 13 21
43. 100ml 4 2 1 v v Bio Gel P 2 2 6X90cm A Dowex 1 X2 THE CHEAICAL TIAES 2 6X 20 cm TSK gel Amido 80 4 6 X 250 mm HPLC 15mM pH 5 2 50 80 2 40 57 5 80 3 HA 1 HA 2 HA 3 H NMR HA 2 3
44. 3 3 95 ee o H be Ru cat SR 3 CHezCHOH 0am se 30 Ru cat RuC Sxybinapl dalpenl KOkBu SK 2000 11 000 H CHs 96 yleld 95 ee CaHs 99 7 yield 96 ee A 4 2 1 Ru eat 1 4 Gy RF CHzCHOH R Sam so gt 99 yeld Het hetero aromatic ring Ru cat AuCiaftR y xyfbinap A dalpen KOtBu SC 2000 40000 OH Te gt ym 99 ee 97 ee THE CHEAICAL TIAES o CHa Rucat am CHukCHOH 25 oH oh PiolSO2 on oH AN N S Ow 0 99 7 ee 97 ee 98 ee 96 ee oH OH oH oH NN NN NS 96 ee 94 ee 99 6
45. Recent Progress of Noyori s Catalysis THE CHEMICAL TIAAES QH R ee gH carbonyj sefectivity gt 9896 CHS 86 94 OY Rc PCHgsC 95 ey CH 91 om pO 90 94 CH22 98 mpCHsO 88 92 oH OH RE 0 Ha carbonyi selectvly 99 carbony selectivity 299 carbony selectiity gt 99 90 ee 92 ee 94 ee CH2 a 81 Mo 90 ONS TA Ar CeHs 89 BINAP 8 9 DPEN 9 DAIPEN Rucat RuCkK bInap dm0 5 9 DPEN or y DAIPEN KOH 1 1 2 ketone Ru 500 11 30 C 1 DPEN DAIPEN 1 1 2 1 2 RuCll A tolbinap i R R dpen No 1 2002 S BINAP R BINAP RR
46. BERID BA 6 4 3 BA 6 4 4 NPO BA NPO 5
47. 5 430ppm 2 052ppm HA 3 N N 2 N Gal 1 4GclINAc 2 A 3 1 UDP 1 N N UDP 1960 UDP GicNAc H NMR UDP 7 964ppm 5 974ppm 4 385ppm
48. RQ PO 5 120mg 5 R2 0 983 46 y 0 464 1 03x mg s 0 56 100 150 200 RGQ mg 5 RQ 59 amp R2 0938 23 50 y 3 14 131x 1 30 Dh 20 10 0 10 20 30 40 RQ ppm 6 6 12 4 14 26 23 6
49. 20 100 18 No 1 2002 5 b 6 8 3 3 2 3 1 10 15 20 100 82 734mg 9 0 14 0 20 1 4 0 620
50. 4 17 2 Medicines Based on Genetic Information Vi Promotion of Bio industry Osaka area No 1 2002 THE CHEAICAL TIMES 5 5 7 7 7 8 2
51. N TI NMR 9C NMR N 4 HA 3 DzO HSQC H NMR C NMR HSQC Heteronuclear Simple Quantum Coherence THE CHEAICAL TIAES GlcNAc o HA 3 MALDI TOFmass HA 3 m z 226 231 393 GlcNAc al m z 226 MT 5 HA 3 m z 231 393 GlcNAc o1 m z 226 5 m z 226 5 5
52. 7 3500 5000 8 2200 3600 2000 3500 60007500 3000 4500 5000 7000 NO3mg L 96 b sooo ES a eo st so LL ST 40 dm gt N 100 50 5 225mg 90 20 4 8 9 5 20 30 4 4 1 2 3 4 5 6 7 10 12 18 35 33 128 48 725 20 3 5 9 8 32 1
53. R TolBINAP R RR DPEN S DPEN 2 X 1 2 TolBINAP DPEN RuClai A tolbinap S dpen 1 RuCls tolbinap dpen iorson No 1 2002 2 7A 2 8A 3 0A BINAP TolBINAP Xyi1BINAP 1 99 ee 9 Qn Ru eat 9 CCHOH ea 1 1 10 atm 26 30 C 97 100 yieia Rucat RuCbI S xyblnapl dIamine KO Bu SC 500 100 0
54. 49 195 202 2000 a 0 1 19 Nakamura T S Amikawa T Harada T Saito 1 Arai and 0 0 6 0 6 lt 6 T Urashima Biochim Biophys Acta 1525 13 18 2001 20 Kobata A Biochim Biophys Res_ Commsn 7 346 350 1962 21 Parkkinen J and J Finne Methods Enzymol 138 289 300 G987 22 Iwanowitsch A H Friebolin R Carganico M Errenst G Weisschaar H Brunner and H Mann Biol Chem 379 i i 7137 741 1998 23 Saito T T Itoh and S Adachi Biochim Biophys Acta 801 147 150 1984 24
55. MEW 5 tt 88 M 30 SE P28 3U1JdS 7 No 1 2002 THE HEAAICAL TIAES 9 1 1 gt 11 M 0 5B gt 1 Y 1 7 1
56. S BINAP RR R BINAP S 2 BINAP DIOP CHIRAPHOS f2 BINAP DPEN DAIPEN 2 2mg RuCl2 E binap daipen 48 601g 80 ee
57. 19 THE CHEAICAL TIAES No 1 2002 VI 1 milk oligosaccharides 9 9 55 9 7 100 1
58. 21 THE CHEMICAL TIMES No 1 2002 HA 3 5 430 ppm 4 486ppm 2 1 1 4 486ppm 1 s 18 5 5 5 4 6 0 sa 4 0 N Gal 81 3 2 225 Acetone 2 052 GlcNAc NAc CH 3 0 2 0 1 0 Chemical Shifts ppm 3 HA 3 DzO 600MHz H NMR a 8 2 2 HA 3 Gal 81 4 2 5 430ppm eg 1 c
59. 1984 994 2 2 0 CS 2 3 7e Chemical Times No 167 3 9 1998 4 7 e Chemical Times No 173 2 8 1999 5 The Chemical Times No 175 3 8 2000 5 6 The Chemical Times No 176 18 21 en 7 The Chemica Times No 177 11 Ma 7 Chemics THmes No 177 1116 8 81 80 82 1993 9 Messer M 33 816 824 1995 10 46 211 220 gt 1997
60. 7 4 100 Y 0 97X 0 66 0 929 29 Y X RQ b 1 2 100 RQ Y 0 985X 159 0 981 31 5 Y X RQ a 2 3
61. 2001 p 387 2001 25 Ebner K E and F L Schanbacher In Lactation B L Larson and V R Smith Vol 2 pp 77 109 Academic Press New York 1974 lt gt 2002 2001 W 12 103 0023 3 2 8 03 3279 1751 FAX 03 3279 5560 Cec http www kanto co jp 14 1 1 24
62. 9 68Y V Y OdN a 47 68 Y NvdyT 7 1 7 YZIS CYL id39 MBE EG ELLIE BTUndS 1 a 9 V oN 68 1 RR 8 5 27 14 No 1 2002 THE CHEAICAL TIA
63. Neu5Ac g2 3 Gal 81 4 Glc EC E 3 75 SS 3 amp a 70 8 5 2 65 8 lt 2 60 lt 0 10 20 30 40 50 60 Retention Time min 2 HPLC Tosoh CCPM II intelligent TSk gel Amido 8 4 6X250mm pore size 80um particle size 5 m 15mM buffer pH 5 2 50 80 40C 80 57 5 HA 1 HA 3 HA 3 H NMR 3 H 3 eq ax 1 8pprm 2 7ppm
64. 5735 5738 9 Palmer M J Wills M Terahedron Asymmetry 1999 10 2045 2061 10 a Alonso D A Brandt P Nordin S J M Andersson P G J Am Chem Soc 1999 121 9580 9588 11 Casey C P Singer S W Powell D R Hayashi R K Kavana M 1 Am Chem Soc 2001 123 1090 1100 THE CHEAICAL TIAAES No 1 2002 6 8 2002 5
65. 8 _ 0 RI 0 11 37 401 403 1999 2 57 619 620 1999 13 583 1155 1160 1999 8 14 48 199 2051999 sah 0 Re 15 33 11 13 2000 N g1 16 38 3447 3451 2000 W 2 17 50 50 38 57 2000 18
66. 00 dlmmine 0 0 R Nz Ar 3 54CHa zCaH SrXyIBINAP R CHgzCH DAIPEN OH on oH 97 yled 99 ee 98 yield 100 ee 100 yleld 97 ee 99 9 yield 99 ee 9 9 2 AM SM 99 9 yield 99 6 ee 99 7 yleld 99 eo 100 yekd 99 6 ee 100 yleld 100 ee 9H or on 6 5 9 98 J y Ss i CeHs TcFs 100 yiekd 99 ee 100 yield 99 8 ee 100 yield 99 ee 100 yield 96 ee 2 E 909 ee S 6 2 3 3 2 THE CHEAICAL TIAAES RS O RZ_oH Rucat Rr Rt Hz OR PD a 2 10 80 atm Ben FR Ru cat RuClal yxyibinap diamine K2C04 dlamine DAIPEN or 8 9 1 2 Cyclohexanediamine SC 2000 100 000 gH on 9H ct ci rc 100 yleld 97 ee 100 yleld 86 ee 98 yleld 97 ee oH 100 yleld 90 ee 100 yled 93 oe 99 yield 100 ee 9 9H 99 9 eld 99 ee 100 yield 99 ee
67. 2 3 1 10 15 5 100 5 225 mg 9 17 1 500mg z 88 1 85 2 34 1 3 10 23 4 1 4 0 801 THE CHEAICAL TIAES
68. 2 19 90 8 10 3 1ZC P2 t t C P 1 1 3 4 5 6 7 1 8 10 b 6 8 3 3
69. ES II RQ 1 1 RQ RQ RQ RQ
70. ISSN MO KANTO CHEMICAL CO 2002 NO 1 183 CMCAL TMES 6 i RQ WW ceooovahsosedeaeao2 NGKAUeSoven2rHAGSORERSRASARz2 YA09SSGAYcGranezoeesstaaySRgsireeooa 24 Dh ES SR EE PES THE CHEAICAL TIMES No 1 2002 IT
71. M Ikehira H Yokozawa T Noyori R Org Lett 2000 2 659 662 k Ohkuma T Ishii D Takeno H Noyori R J Am Chem Soc 2000 122 6510 6511 1 Ohkuma T Koizumi M Yoshida M Noyori R Org Lett 2000 2 1749 1751 m Mikami K Korenaga T Ohkuma T Noyori R 4Angew Chem Int Ed Engl 2000 39 3707 3710 n Noyori R Ohkuma T Amgew Chem Int Ed Engl 2001 40 40 73 o Noyori R Koizumi M Ishii D Ohkuma T Pure Appl Chem 2001 73 227 232 p Ohkuma T Takeno H Honda Y Noyori R Adv Synth Catal 2001 343 369 375 2 Burk M J Hems W Herzberg D Malan C Zanotti Gerosa A Org Lett 2000 2 4173 4176 3 Jiang Q Jiang Y Xiao D Cao P Zhang X Angew Chem Int Ed Engl 1998 37 1100 1103 3 a Abdur Rashid K Lough A J Morris R H Organo metallics 2000 19 2655 2657 b Abdur Rashid K Lough A J Morris R H Organometallics 2001 20 1047 1049 c Abdur Rashid K Faatz M Lough A J Morris R H J Am Chem Soc 2001 123 7473 7474 5 Hartmann R Chen P Angew Chem Int Ed Engl 2001 40 3581 3854 THE CHEMICAL TIMES 6 a Hashiguchi S Fujii A Takehara J Ikariya T Noyori R 7 Am Chem Soc 1995 117 7562 7563 b Takehara J Hashiguchi S Fujii A Inoue S Ikariya T Noyori R J Chem Soc Chem Commun 1996 233 234 c Gao J X Ikariya T
72. Noyori R Organometallics 1996 15 1087 1089 d Fujii A Hashiguchi S Uematsu N Ikariya T Noyori R 7 Am Chem Soc 1996 118 2521 2522 e Uematsu N Fujii A Hashiguchi S Ikariya T Noyori R J Am Chem Soc 1996 118 4916 4917 f Haack EK J Hashiguchi S Fujii A Ikariya A Noyori R Angew Chem Int Ed Engl 1997 36 285 288 g Hashiguchi S Fujii A Haack K J Matsumura K Ikariya T Noyori R Angew Chem Int Ed Engl 1997 36 288 290 h Matsumura K Hashiguchi S Ikariya T Noyori R Am Chem Soc 1997 779 8738 8739 i Noyori R Hashiguchi S Acc Chem Res 1997 30 97 102 5 Yamakawa M Ito H Noyori KR Am Chem Soc 2000 122 1466 1478 k Yamada I Noyori R Org Lett 2000 2 3425 3427 1 Noyori R Yamakawa M Hashiguchi S J Org Chem 2001 66 7931 7944 7 a Murata K Ikariya T Noyori R J Org Chem 1999 64 2186 2087 b Murata K Okano K Miyagi M Iwane H Noyori R Ikariya T Org Lett 1999 1 1119 1121 c Okano K Murata K Ikariya T Tetrahedron Lett 2000 41 9277 9280 d Koike T Murata K Ikariya T Org Lett 2000 2 3833 3836 e Watanabe M Murata K Ikariya T submitted for publication 8 a Kanada R M Taniguchi T Ogasawara K J Chem Soc Chem Commun 1998 1755 1756 b Iura Y Sugahara T Ogasawara K Tetrahedron Lett 1999 40
73. RQ 1g 0 002N 200m amp 75mg 100g P 1 6mg x RQ 100 R2 0 994 11 1 y 0 986 1 03x 80 9 60 A 40 kn 20 0 0 20 40 60 80 100 RQ mg 100g 4 RQ THE HEAICAL TIMES 4
74. ee 99 8 ee QH OH oH OH AN N CHsz 0 9 2 2 100 ee 19 ee 92 ee 9 2 3 5 RM HH RR CHszCHOH 25 Ru eat RuC xybinaPI daipenl KOFBu SC 1000 2000 0 NeHs NH9CeHs om Nchas 99 yleld 92 ee 93 yleld 81 e0 90 yield 93 ee OH OH OH oNoHoOoHD NitCoceHd ncrscocyg 97 yleld 99 ee 929 yleld 95 ee 96 yield 99 8 ee OH OH COCOCH cm NoHstCoOcHs cm Nch YOCHs 98 yleld 99 oe 94 yleld 99 ee 6 2 98
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