| Synthesis of fluorine-containing bioisosteres corresponding to phosphoamino acids and dipeptide units. | |
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MedLine Citation:
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PMID: 15054894 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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It has been shown that fluorinated analogues of naturally occurring biological active compounds including amino acids often exhibit unique physiological activity. Among wide varieties of fluorine-containing amino acids, nonhydrolyzable phosphoamino acids possessing a substituent of the difluoromethylene (CF(2)) unit for the phosphoryl ester oxygen are of value in the medicinal and biological fields. We have engaged in the synthesis of these classes of nonhydrolyzable phosphoamino acids corresponding to pTyr 3, pSer 4, and pThr 5 with their incorporation into peptides using newly developed deprotecting procedures. In this article, stereoselective synthesis of the CF(2)-substituted pThr mimetics and development of a two-step deprotecting methodology for the nonhydrolyzable analogues are reviewed. In the course of the above synthetic study, we found that gamma,gamma-difluoro-alpha,beta-enoates were reduced to gamma-fluoro-beta,gamma-enoates by organocopper reagents and then applied to the synthesis of (Z)-fluoroalkene dipeptide isosteres, which have served as potential dipeptide mimetics having structural as well as electrostatic similarity to the parent peptide bonds. Furthermore, mechanistic investigation of the organocopper-mediated reduction led us to development of a SmI(2)-mediated approach toward the synthesis of the fluoroalkene isosteres. |
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Authors:
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Akira Otaka; Etsuko Mitsuyama; Junko Watanabe; Hideaki Watanabe; Nobutaka Fujii |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Review |
Journal Detail:
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Title: Biopolymers Volume: 76 ISSN: 0006-3525 ISO Abbreviation: Biopolymers Publication Date: 2004 |
Date Detail:
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Created Date: 2004-03-31 Completed Date: 2004-05-13 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0372525 Medline TA: Biopolymers Country: United States |
Other Details:
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Languages: eng Pagination: 140-9 Citation Subset: IM |
Copyright Information:
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Copyright 2004 Wiley Periodicals, Inc. Biopolymers (Pept Sci), 2004 |
Affiliation:
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Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. aotaka@pharm.kyoto-u.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Biomimetic Materials
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chemical synthesis,
chemistry Dipeptides / chemistry* Hydrocarbons, Fluorinated / chemical synthesis* Phosphoamino Acids / chemical synthesis, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Dipeptides; 0/Hydrocarbons, Fluorinated; 0/Phosphoamino Acids |
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