On-resin macrocyclization of peptides via intramolecular SnAr reactions.

Abstract:

:On-resin macrocyclization via an SNAr reaction is employed in the synthesis of tocinoic acid analogs. Specifically, an N-terminal nitrofluorobenzene is attacked by a nucleophilic C-terminal sidechain. The remaining nitro group can be reduced and acylated. NMR is used to compare the conformation of the new macrocyclic peptides to tocinoic acid.

journal_name

Bioorg Med Chem Lett

authors

Fotsch C,Kumaravel G,Sharma SK,Wu AD,Gounarides JS,Nirmala NR,Petter RC

doi

10.1016/s0960-894x(99)00356-x

subject

Has Abstract

pub_date

1999-08-02 00:00:00

pages

2125-30

issue

15

eissn

0960-894X

issn

1464-3405

pii

S0960894X9900356X

journal_volume

9

pub_type

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