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Synthesis of paromomycin derivatives modified at C(5'') to selectively target bacterial rRNA.

Authors
Type
Published Article
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
342
Issue
3-4
Pages
499–519
Identifiers
PMID: 17049499
Source
Medline

Abstract

The furanosyl moiety (ring III) of C(6')-deoxyparomomycin and paromomycin was modified in search of aminoglycoside antibiotics with altered selectivity. The key intermediates were the N-Boc-protected derivative of C(6')-deoxyparomomycin and the benzylidene-protected paromomycin. Their H(2)C(5'')-OH group was oxidised with trichlorocyanuric acid or [bis(acetoxy)iodo]benzene in the presence of catalytic amounts of TEMPO to yield the corresponding aldehydes and acids, which were transformed into the protected alkoxy imines, amides and the amine. Standard deprotection gave the title compounds derived from C(6')-deoxyparomomycin and derived from paromomycin that proved less active than paromomycin and its C(6')-deoxy analogue.

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