Stereocontrolled synthesis of hydroxymethylene phosphonate analogues of phosphorylated tyrosine and their conversion to monofluoromethylene phosphonate analogues

被引：46

作者：

Yokomatsu, T

Yamagishi, T

Matsumoto, K

Shibuya, S

机构：

[1] TOKYO UNIV PHARM & LIFE SCI, SCH PHARM, HACHIOJI, TOKYO 19203, JAPAN

[2] TAISHO PHARMACEUT CO LTD, RES CTR, OMIYA, SAITAMA 330, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 36期

关键词：

D O I：

10.1016/0040-4020(96)00671-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of protected variants 13 and 15 of HPmp 2, a mimic of phosphorylated tyrosine, was achieved through either chiral-auxiliary assisted or chiral heterobimetal catalyzed stereoselective hydrophosphonylation of 4-formyl-L-phenylalanine derivative 7. Fluorination of HPmp, derivatives 13 and 15 thus obtained was carried out to give FPmp derivatives 16 and 17. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：11725 / 11738

页数：14

共 28 条

[1] AKAMATSU M, 1995, J MED CHEM, V38, P4270
[2] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex
Arai, T
Bougauchi, M
Sasai, H
Shibasaki, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 2926 - 2927
[3] SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 913 - 917
[4] 4'-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides
Burke, TR
Ye, B
Akamatsu, M
Ford, H
Yan, XJ
Kole, HK
Wolf, G
Shoelson, SE
Roller, PP
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) : 1021 - 1027
[5] NONHYDROLYZABLE PHOSPHOTYROSYL MIMETICS FOR THE PREPARATION OF PHOSPHATASE-RESISTANT SH2 DOMAIN INHIBITORS
BURKE, TR
SMYTH, MS
OTAKA, A
NOMIZU, M
ROLLER, PP
WOLF, G
CASE, R
SHOELSON, SE
[J]. BIOCHEMISTRY, 1994, 33 (21) : 6490 - 6494
[6] PREPARATION OF FLUORO-4-(PHOSPHONOMETHYL)-D,L-PHENYLALANINE AND HYDROXY-4-(PHOSPHONOMETHYL)-D,L-PHENYLALANINE SUITABLY PROTECTED FOR SOLID-PHASE SYNTHESIS OF PEPTIDES CONTAINING HYDROLYTICALLY STABLE ANALOGS OF O-PHOSPHOTYROSINE
BURKE, TR
SMYTH, MS
NOMIZU, M
OTAKA, A
ROLLER, PP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1336 - 1340
[7] PREPARATION OF AN ANGIOTENSIN-I ANALOG CONTAINING A PARA-PHOSPHONOMETHYL-L-PHENYLALANINE RESIDUE VIA ASYMMETRIC-SYNTHESIS OF TERT-BOC-PARA-DIMETHYLPHOSPHONOMETHYL-L-PHENYLALANINE
CUSHMAN, M
LEE, ES
[J]. TETRAHEDRON LETTERS, 1992, 33 (09) : 1193 - 1196
[8] INHIBITION OF SH2 DOMAIN PHOSPHOPROTEIN ASSOCIATION BY A NONHYDROLYZABLE PHOSPHONOPEPTIDE
DOMCHEK, SM
AUGER, KR
CHATTERJEE, S
BURKE, TR
SHOELSON, SE
[J]. BIOCHEMISTRY, 1992, 31 (41) : 9865 - 9870
[9] DOW RL, 1994, SYNLETT, P293
[10] RECOGNITION OF A HIGH-AFFINITY PHOSPHOTYROSYL PEPTIDE BY THE SRC HOMOLOGY-2 DOMAIN OF P56(LCK)
ECK, MJ
SHOELSON, SE
HARRISON, SC
[J]. NATURE, 1993, 362 (6415) : 87 - 91

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