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Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas

  • Lee, Jong-Soo (Department of Seafood Science and Technology, Institute of Marine Industry, Gyeongsang National University) ;
  • Satake, Masayuki (Graduate School of Agricultural Science, Tohoku University) ;
  • Horigome, Yoichi (Graduate School of Agricultural Science, Tohoku University) ;
  • Oshima, Yasukatsu (Graduate School of Agricultural Science, Tohoku University) ;
  • Yasumoto, Takeshi (Graduate School of Agricultural Science, Tohoku University)
  • Received : 2011.12.06
  • Accepted : 2012.02.08
  • Published : 2012.03.30

Abstract

A new cyclic peptide (six-membered amino acid), gamakamide-E (L-Leu-L-Met (SO)-L-Me-Phe-L-Leu-D-Lys-L-Phe), was isolated as a strongly bitter tasting compound from cultured oysters, Crassostrea gigas. The molecular formula of $C_{43}H_{61}N_7O_8S$ was deduced from high resolution fast atom bombardment mass spectrometry (HR FAB-MS) ($[M+H]^+$ m/z 836.4356 ${\Delta}$= -2.4 mmu). Its unique structure including a hydantoin structure was firstly elucidated by nuclear magnetic resonance (NMR) analysis. Stereochemistries of constituent amino acids were determined by chiral high performanced liquid chromatography analysis of natural and synthesized peptides.

Keywords

References

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  1. Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities vol.23, pp.2, 2018, https://doi.org/10.3390/molecules23020306