Fisheries and Aquatic Sciences

The Korean Society of Fisheries and Aquatic Science (한국수산과학회)
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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
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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.

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References

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