Sungsanpin, a lasso peptide from a deep-sea streptomycete

Title
Sungsanpin, a lasso peptide from a deep-sea streptomycete
Authors
엄수현김영주권혁남He Wen김성환권학철박성혁신종헌오동찬
Issue Date
2013-05
Publisher
Journal of natural products
Citation
VOL 76, NO 5, 873-879
Abstract
Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey’s reagents and 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly1-Phe-Gly-Ser-Lys-Pro-Ile-Asp8-) that form a cyclic peptide and seven amino acids (-Ser9-Phe-Gly-Leu-Ser-Trp-Leu15) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.
URI
http://pubs.kist.re.kr/handle/201004/45215
ISSN
01633864
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