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An expedient synthesis of N(alpha)-protected-L-tetrahydrofuranylglycine and its application in the synthesis of novel substrate based inhibitors of HIV-1 protease.

An expedient synthesis of N(alpha)-protected-L-tetrahydrofuranylglycine and its application in the synthesis of novel substrate based inhibitors of HIV-1 protease.

Authors :
Rajesh S
Ami E
Kotake T
Kimura T
Hayashi Y
Kiso Y
Source :
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2002 Dec 16; Vol. 12 (24), pp. 3615-7.
Publication Year :
2002

Abstract

Z- and Fmoc-L-tetrahydrofuranylglycines have been obtained from L-vinylglycine through dipolar cycloaddition reaction, and its Fmoc derivative has been applied in the synthesis of modified S9 and S10 substrates of HIV-1 protease. These compounds mostly acted as strong inhibitors, rather than substrates, of the protease, probably due to the favourable interactions of the tetrahydrofuranylglycine moiety at the S(2) site.

Details

Language :
English
ISSN :
0960-894X
Volume :
12
Issue :
24
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry letters
Publication Type :
Academic Journal
Accession number :
12443788
Full Text :
https://doi.org/10.1016/s0960-894x(02)00781-3