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Synthesis of new analogs of echinocandin B by enzymatic deacylation and chemical reacylation of the echinocandin B peptide: synthesis of the antifungal agent cilofungin (LY121019)

Debono, M.; Abbott, B.J.; Fukuda, D.S.; Barnhart, M.; Willard, K.E.; Molloy, R.M.; Michel, K.H.; Turner, J.R.; Butler, T.F.; Hunt, A.H.

Journal of Antibiotics 42(3): 389-397

1989


ISSN/ISBN: 0021-8820
PMID: 2708132
DOI: 10.7164/antibiotics.42.389
Accession: 041522565

The antifungal antibiotic, echinocandin B (ECB), was modified by a sequential procedure in which the initial step involved enzymatic removal of the native N-linoleoyl group from the N-terminus using an Actinoplanes utahensis culture. The resulting product, ECB nucleus, was reacylated using active esters or acid halides of various substituted acids to give a series of ECB analogs. These analogs possessed anti-Candida activity both in vitro and in vivo (mice). Other studies have shown that one of these, cilofungin, the 4-n-octyloxybenzoyl-ECB analog (LY121019), has excellent anti-Candida activity, low toxicity and is superior to other available antifungal antibiotics.

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