期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 18, 页码 6898-6907出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061044e
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资金
- Intramural NIH HHS Funding Source: Medline
Seven new depsipeptides, termed largamides A-G (1-7), and one new cyclic peptide, largamide H ( 8), have been isolated from the marine cyanobacterium Oscillatoria sp. Their structures were determined by NMR and ESI-MS techniques. The absolute configurations were assigned using LC-MS, chiral HPLC, and combined analysis of homonuclear and heteronuclear (2,3)J couplings, along with ROE data. Largamides, isolated from a single homogeneous cyanobacterial collection, represent three different structural classes of peptides. Largamides A-C (1-3) are characterized by the unusual occurrence of a senecioic acid unit, while largamides B ( 2) and C ( 3) possess in addition the rare 2-amino-5-(4'-hydroxyphenyl) pentanoic acid (Ahppa) and the novel 2-amino-6-(4'-hydroxyphenyl) hexanoic acid ( Ahpha), respectively. Largamides D-G (4-7) are the first 3-amino-6-hydroxy-2-piperidone acid (Ahp)-containing depsipeptides reported with the rare Ahppa unit. Largamide H (8) is a unique cyclic peptide displaying a new 2,5-dihydroxylated beta-amino acid moiety, a methoxylated derivative of Ahppa, and two residues of the nonstandard 2,3-dehydro-2-aminobutanoic acid (Dab). Largamides D-G (4-7) inhibited chymotrypsin with IC50 values ranging between 4 and 25 mu M.
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