Efficient Synthesis of Fmoc-Protected Phosphinic Pseudodipeptides: Building Blocks for the Synthesis of Matrix Metalloproteinase Inhibitors

被引：10

作者：

Bhowmick, Manishabrata ^{[1
]}

Sappidi, Ravinder R. ^{[1
]}

Fields, Gregg B. ^{[2
]}

Lepore, Salvatore D. ^{[1
]}

机构：

[1] Florida Atlantic Univ, Dept Chem & Biochem, Boca Raton, FL 33431 USA

[2] Univ Texas Hlth Sci Ctr San Antonio, Dept Biochem, San Antonio, TX 78229 USA

来源：

BIOPOLYMERS | 2011年 / 96卷 / 01期

关键词：

phosphinic pseudodipeptides; matrix metalloproteinase inhibitors; MMPI; peptide synthesis; phosphinates; SOLID-PHASE SYNTHESIS; 1-AMINOALKYLPHOSPHINIC ACIDS; AMINO-ACIDS; ISOSTERES; PEPTIDES; TARGETS;

D O I：

10.1002/bip.21425

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A convenient route for the synthesis of Finoc-protected phosphinic dipeptide building blocks is described. The protected amino acid isosteres benzyloxycarbonyl aminomethyl phosphinic acid (glycine surrogate), benzyl alpha-isopropyl acrylate (valine surrogate), and benzyl alpha-isobutyl acrylate (leucine surrogate) were synthesized starting from commercially available materials. Reaction of either the valine or leucine surrogate with bis(trimethylsilyl) phosphonite generated the pseudodipeptide bond. The synthesis concluded with an efficient one-pot three-step procedure involving a bis-deprotection of the N- and. C-termini under catalytic hydrogenation conditions followed by selective capping of the N-terminus with an Fmoc group to yield either Fmoc-NHCH2PO(OAd)CH2CH(Pr-i)CO2H or Fmoc-NHCH2PO(OAd)CH2CH(Bu-i)CO2H. (C) 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 1-3, 2011.

引用

页码：1 / 3

页数：3

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