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Design and Synthesis of Guanidinoglycosides Directed against the TAR RNA of HIV-1

✍ Scribed by Min Wang; Peng-Fei Tu; Zhi-Dong Xu; Xiao-Lin Yu; Ming Yang

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
161 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Replication of human immunodeficiency virus type 1 (HIV‐1) requires specific interactions of the Tat protein with the transactivation responsive region (TAR) RNA. Tat‐TAR RNA Interaction is mediated by a short arginine‐rich domain of the protein. Disruption of this interaction could, in theory, create a state of complete viral latency. Here, four novel 6‐amino‐6‐deoxytrehalose guanidinoglycoside derivatives (10 and 13–15) as target molecules have been designed to bind to TAR RNA for blocking the interaction of Tat‐TAR RNA. They were obtained by coupling 6‐amino‐6‐deoxy‐α,α‐trehalose (6) with the protected amino acids, deprotection by catalytic hydrogenation, followed by guanidinylated with S‐methylisothiourea sulfate. Their abilities to inhibit Tat‐TAR RNA interaction were determined by a Tat‐dependent HIV‐1 long terminal repeats (LTR)‐driven chloramphenicol acetyltransferase (CAT) assays.

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