Peptide inhibitors of aspartic proteinases with hydroxyethylene isostere replacement of peptide bond. I. Preparation of four diastereoisomeric (2R or 2S,4R or 4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic acids

被引：14

作者：

Litera, J ^{[1
]}

Budesinsky, M ^{[1
]}

Urban, J ^{[1
]}

Soucek, M ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1998年 / 63卷 / 02期

关键词：

hydroxyethylene isostere; gamma-lactones; 5-amino-2-benzyl-4-hydroxy-6-phenylhexanoic acids; diastereoisomers; transition state analogues; peptidomimetics;

D O I：

10.1135/cccc19980231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By two separate routes were prepared four diastereoisomers of (2R or 2S,5R or SS)-3-benzyI-5-{(1S)[(tert-butoxycarbonyl)amino]-2-phenylethyl}tetrahydrofuran-2-one (11, 12, 17 and 18). Since the furanones were derived from (S)-phenylalanine, absolute configurations of all chiral carbon atoms could be deduced from their H-1 NMR spectra. The furanones were easily hydrolyzed to four (2R or 2S,4R or 4S,5S)-2-benzyl-5-[(tert-butoxycarbony)amino]-4-hydroxy-6-phenylbutanoic acids (20-23), hydroxyethylene isosteres of Phe-Phe peptide bond.

引用

页码：231 / 244

页数：14