Document Detail


Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl D-phenylalanine derivatives.
MedLine Citation:
PMID:  20031409     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Some D-amino acids such as d-tryptophan and D-phenylalanine are well known as naturally-occurring sweeteners. Photoreactive D-phenylalanine derivatives containing trifluoromethyldiazirinyl moiety at 3- or 4-position of phenylalanine, were designed as sweeteners for functional analysis with photoaffinity labeling. The trifluoromethyldiazirinyl D-phenylalanine derivatives were prepared effectively with chemo-enzymatic methods using L-amino acid oxidase and were found to have potent activity toward the human sweet taste receptor.
Authors:
Katsuyoshi Masuda; Ayako Koizumi; Takumi Misaka; Yasumaru Hatanaka; Keiko Abe; Takaharu Tanaka; Masaji Ishiguro; Makoto Hashimoto
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-12-11
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  20     ISSN:  1464-3405     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2010 Feb 
Date Detail:
Created Date:  2010-02-03     Completed Date:  2010-09-20     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  1081-3     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2009 Elsevier Ltd. All rights reserved.
Affiliation:
Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan.
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MeSH Terms
Descriptor/Qualifier:
Cell Line
Crystallography, X-Ray
Humans
Phenylalanine / chemical synthesis*,  metabolism*
Photoaffinity Labels / chemical synthesis*,  metabolism*
Protein Structure, Tertiary
Receptors, G-Protein-Coupled / chemistry,  metabolism*
Sweetening Agents / metabolism
Taste Buds / chemistry,  metabolism*
Chemical
Reg. No./Substance:
0/Photoaffinity Labels; 0/Receptors, G-Protein-Coupled; 0/Sweetening Agents; 0/taste receptors, type 1; 63-91-2/Phenylalanine

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