Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies

被引：22

作者：

Yao, ZJ ^{[1
]}

Gao, Y ^{[1
]}

Voigt, JH ^{[1
]}

Ford, H ^{[1
]}

Burke, TR ^{[1
]}

机构：

[1] NCI, Med Chem Lab, Div Basic Sci, NIH, Bethesda, MD 20892 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 10期

关键词：

amino acids and derivatives; asymmetric synthesis; molecular design; peptide analogues/mimetics;

D O I：

10.1016/S0040-4020(99)00076-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.

引用

页码：2865 / 2874

页数：10

共 21 条

[1]

ALBERT A, 1962, IONIZATION CONSTANTS

[2]

Burke TR, 1997, CURR PHARM DESIGN, V3, P291

[3] 4'-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides [J].

Burke, TR ;

Ye, B ;

Akamatsu, M ;

Ford, H ;

Yan, XJ ;

Kole, HK ;

Wolf, G ;

Shoelson, SE ;

Roller, PP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1021-1027

[4] Enantioselective synthesis of nonphosphorus-containing phosphotyrosyl mimetics and their use in the preparation of tyrosine phosphatase inhibitory peptides [J].

Burke, TR ;

Yao, ZJ ;

Zhao, H ;

Milne, GWA ;

Wu, L ;

Zhang, ZY ;

Voigt, JH .

TETRAHEDRON, 1998, 54 (34) :9981-9994

[5]

BURKE TR, IN PRESS BIOORG MED

[6] O-(carboxydifluoromethyl)-L-tyrosine:: Design and synthesis of a novel non phosphorous-containing phosphotyrosine isostere [J].

Fretz, H .

TETRAHEDRON, 1998, 54 (19) :4849-4858

[7] IMPROVED SYNTHESIS OF [PARA-PHOSPHONO AND PARA-SULFO]METHYLPHENYLALANINE - RESOLUTION OF [PARA-PHOSPHONO-METHYLPHENYLALANINE, PARA-SULFO-METHYLPHENYLALANINE, PARA-CARBOXY-METHYLPHENYLALANINE AND PARA-N-HYDROXYCARBOXAMIDO-]METHYLPHENYLALANINE [J].

GARBAYJAUREGUIBERRY, C ;

MCCORTTRANCHEPAIN, I ;

BARBE, B ;

FICHEUX, D ;

ROQUES, BP .

TETRAHEDRON-ASYMMETRY, 1992, 3 (05) :637-650

[8]

GILMER T, 1994, J BIOL CHEM, V269, P31711

[9] Structural basis for inhibition of the protein tyrosine phosphatase 1B by phosphotyrosine peptide mimetics [J].

Groves, MR ;

Yao, ZJ ;

Roller, PP ;

Burke, TR ;

Barford, D .

BIOCHEMISTRY, 1998, 37 (51) :17773-17783

[10] PREPARATION OF ENANTIOMERICALLY PURE PROTECTED 4-OXO-ALPHA-AMINO ACIDS AND 3-ARYL-ALPHA-AMINO ACIDS FROM SERINE [J].

JACKSON, RFW ;

WISHART, N ;

WOOD, A ;

JAMES, K ;

WYTHES, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3397-3404

← 1 2 3 →