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Conformational control of cyclosporin through substitution of the N-5 position. A new class of cyclosporin antagonists.

Abstract：

:Cyclosporin A (CsA) can be regiospecifically alkylated at the NH of Val-5 with reactive bromides in the presence of phosphazene-base P4-t-Bu to yield derivatives 2-5. These are devoid of immunosuppressive activity in vitro but they have binding affinity for cyclophilin A (CypA) similar to that of CsA and thus represent a new class of cyclosporin antagonists. 1H NMR (DMSO-d6) studies have shown that the compounds exist in a single, all trans conformation. A comparison of this NMR data with X-ray crystallographic analysis of a CypA/CsA derivative complex demonstrates that the solution structure does not correspond to the bioactive conformation.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Papageorgiou C,Kallen J,France J,French R

doi

10.1016/s0968-0896(96)00204-0

subject

Has Abstract

pub_date

1997-01-01 00:00:00

pages

187-92

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968089696002040

journal_volume

5

pub_type

杂志文章

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