Design and synthesis of a pyridone-based phosphotyrosine mimetic

被引:11
作者
Fu, JM [1 ]
Castelhano, AL [1 ]
机构
[1] Cadus Pharmaceut Corp, Tarrytown, NY 10591 USA
关键词
D O I
10.1016/S0960-894X(98)00503-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel pyridone-based tyrosine analog, 6, has been designed to mimic the binding interaction of SH2 domains with phosphotyrosine (p;Tyr) containing peptides. Synthesis of 6 features a key Pd catalyzed coupling of beta-iodoalanine with phosphonomethyl 4-pyridone triflate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2813 / 2816
页数:4
相关论文
共 20 条
[1]   SYNTHESIS OF 4-PHOSPHONO(DIFLUOROMETHYL)-D, L-PHENYLALANINE AND N-BOC AND N-FMOC DERIVATIVES SUITABLY PROTECTED FOR SOLID-PHASE SYNTHESIS OF NONHYDROLYZABLE PHOSPHOTYROSYL PEPTIDE ANALOGS [J].
BURKE, TR ;
SMYTH, MS ;
OTAKA, A ;
ROLLER, PP .
TETRAHEDRON LETTERS, 1993, 34 (26) :4125-4128
[2]   NONHYDROLYZABLE PHOSPHOTYROSYL MIMETICS FOR THE PREPARATION OF PHOSPHATASE-RESISTANT SH2 DOMAIN INHIBITORS [J].
BURKE, TR ;
SMYTH, MS ;
OTAKA, A ;
NOMIZU, M ;
ROLLER, PP ;
WOLF, G ;
CASE, R ;
SHOELSON, SE .
BIOCHEMISTRY, 1994, 33 (21) :6490-6494
[3]  
CAMBIER JC, 1994, ANNU REV IMMUNOL, V12, P457, DOI 10.1146/annurev.immunol.12.1.457
[4]   WHY IS PHOSPHONODIFLUOROMETHYL PHENYLALANINE A MORE POTENT INHIBITORY MOIETY THAN PHOSPHONOMETHYL PHENYLALANINE TOWARD PROTEIN-TYROSINE PHOSPHATASES [J].
CHEN, L ;
WU, L ;
OTAKA, A ;
SMYTH, MS ;
ROLLER, PP ;
BURKE, TR ;
DENHERTOG, J ;
ZHANG, ZY .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 216 (03) :976-984
[5]   INHIBITION OF SH2 DOMAIN PHOSPHOPROTEIN ASSOCIATION BY A NONHYDROLYZABLE PHOSPHONOPEPTIDE [J].
DOMCHEK, SM ;
AUGER, KR ;
CHATTERJEE, S ;
BURKE, TR ;
SHOELSON, SE .
BIOCHEMISTRY, 1992, 31 (41) :9865-9870
[6]  
EATON SR, 25 NAT MED CHEM S AN
[7]   Discovery of 3-aminobenzyloxycarbonyl as an N-terminal group conferring high affinity to the minimal phosphopeptide sequence recognized by the Grb2-SH2 domain [J].
Furet, P ;
Gay, B ;
GarciaEcheverria, C ;
Rahuel, J ;
Fretz, H ;
Schoepfer, J ;
Caravatti, G .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3551-3556
[8]   Total synthesis of (S,S)-isodityrosine [J].
Jung, ME ;
Starkey, LS .
TETRAHEDRON, 1997, 53 (26) :8815-8824
[9]   BISUBSTRATE REACTION TEMPLATES - EXAMINATION OF THE CONSEQUENCES OF IDENTICAL VERSUS DIFFERENT BINDING-SITES [J].
KELLY, TR ;
BRIDGER, GJ ;
ZHAO, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8024-8034
[10]   Downstream signaling molecules bind to different phosphorylated immunoreceptor tyrosine-based activation motif (ITAM) peptides of the high affinity IgE receptor [J].
Kimura, T ;
Kihara, H ;
Bhattacharyya, S ;
Sakamoto, H ;
Appella, E ;
Siraganian, RP .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (44) :27962-27968