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Synthesis and characterization of the sweetness‐suppressing polypeptide gurmarin and ent ‐Gurmarin
Author(s) -
Ota Masafumi,
Tonosaki Keiichi,
Miwa Kousei,
Fukuwatari Tsutomu,
Ariyoshi Yasuo
Publication year - 1996
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/(sici)1097-0282(199608)39:2<199::aid-bip8>3.0.co;2-k
Subject(s) - chemistry , sweetness , characterization (materials science) , stereochemistry , biochemistry , nanotechnology , taste , materials science
The sweetness‐suppressing polypeptide gurmarin isolated from the leaves of Gymnema sylvestre consists of 35 amino acid residues including three intramolecular disulfide bonds. Herein, the total chemical synthesis of gurmarin was performed by the stepwise fluoren‐9‐ylmethoxy‐carbonyl solid‐phase method, the yield of reduced gurmarin being 1.9% based on the starting amino acid resin. Disulfide formation was carried out in the presence of a redox system of reduced glutathione/oxidized glutathione to give gurmarin in a yield of 35.5%. The product was identical to natural gurmarin by analytical reverse phase high performance liquid chromatography (RP‐HPLC), mass spectroscopy (MS), and peptide mapping, and suppressed the responses to sucrose, D ‐glucose, and L ‐glucose in a rat. The D enantiomer (all D ‐amino acid gurmarin) was also synthesized, and was shown to be the mirror image of gurmarin. Interestingly, the D enantiomer (ent‐gurmarin) also suppressed the responses to sucrose, D ‐glucose, and L ‐glucose in a rat. © 1996 John Wiley & Sons, Inc.