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Selective chemical modifications of polymyxin B.

Abstract：

:Polymyxin B (1) monohydrochloride was converted to the tetra-BOC derivatives 1b and 1c by reaction with di-tert-butyl dicarbonate. The structures of these protected intermediates were established utilizing a degradative sequence that afforded 3 and 5. A method for the deprotection 2,4-dinitrophenylamines to the free amine, utilizing a strongly basic ion-exchange resin, was developed for use in the degradative sequence. The tetra-BOC derivatives 1b and 1c were used to prepare several Polymyxin B derivatives 6-27 at the DAB1 and DAB9-gamma-amine. The antibacterial activity of these selectively functionalized derivatives is reported here.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Weinstein J,Afonso A,Moss E Jr,Miller GH

doi

10.1016/s0960-894x(98)00612-x

subject

Has Abstract

pub_date

1998-12-01 00:00:00

pages

3391-6

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960894X9800612X

journal_volume

8

pub_type

杂志文章

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