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Structure of synechobactins, new siderophores of the marine cyanobacterium Synechococcus sp. PCC 7002
Author(s) -
Ito Yusai,
Butler Alison
Publication year - 2005
Publication title -
limnology and oceanography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.7
H-Index - 197
eISSN - 1939-5590
pISSN - 0024-3590
DOI - 10.4319/lo.2005.50.6.1918
Subject(s) - siderophore , cyanobacteria , synechococcus , fatty acid , residue (chemistry) , nitrilotriacetic acid , amine gas treating , biochemistry , stereochemistry , chemistry , amide , bacteria , biology , organic chemistry , chelation , gene , genetics
The coastal marine cyanobacterium Synechococcus sp. PCC 7002 produces three amphiphilic siderophores, synechobactins A‐C, under iron‐limiting growth conditions. The synechobactins are comprised of a citric acid backbone linked to two 1, 3‐diaminopropane units. The terminal amine of one diaminopropane is acetylated and hydroxylated forming one hydroxamate group. The terminal amine of the other diaminopropane is appended to one of a series of fatty acids and N‐hydroxylated on the fatty acid amide forming the second hydroxamate linkage. Synechobactins A‐C differ among themselves in the identity of the fatty acid residue as dodecanoic acid, decanoic acid, or octanoic acid, respectively. They are the first structurally elucidated siderophores from marine cyanobacteria and are related to schizokinen, a previously identified siderophore that lacks amphiphilic character, isolated from other bacteria including freshwater cyanobacteria.