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J Am Chem Soc. 2002 Mar 20;124(11):2436-7.

Corynebactin and enterobactin: related siderophores of opposite chirality.

Author information

1
Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA.

Abstract

Most species of bacteria employ siderophores to acquire iron. The chirality of the ferric siderophore complex plays an important role in cell recognition, uptake, and utilization. Corynebactin, isolated from Gram-positive bacteria, is structurally similar to enterobactin, a well known siderophore isolated from Gram-negative bacteria, but contains L-theronine instead of L-serine in the trilactone backbone. Corynebactin also contains a glycine spacer unit in each of the chelating arms. A hybrid analogue (serine-corynebactin) has been synthesized. The chirality and relative conformational stability of the three ferric complexes of enterobactin, corynebactin, and the hybrid has been investigated. In contrast to enterobactin, corynebactin assumes a Lambda configuration. However, the ferric serine-corynebactin hybrid forms a racemic mixture, only slightly favoring the Lambda conformation.

PMID:
11890782
DOI:
10.1021/ja016651s
[Indexed for MEDLINE]

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