title: Corynebactin and enterobactin: related siderophores of opposite chirality.
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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA.
authors.forename: Martin E
authors.initials: ME
authors.lastname: Bluhm
authors.forename: Sanggoo S
authors.initials: SS
authors.lastname: Kim
authors.forename: Emily A
authors.initials: EA
authors.lastname: Dertz
authors.forename: Kenneth N
authors.initials: KN
authors.lastname: Raymond
mesh_terms: D004758:Enterobactin / Q000737:chemistry* / Q000378:metabolism / Q000031:analogs & derivatives; D005290:Ferric Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D008968:Molecular Conformation; D017262:Siderophores / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D005290:Ferric Compounds; D017262:Siderophores; D004758:Enterobactin; C044318:corynebactin