Simple and efficient syntheses of Boc- and Fmoc-protected 4( R)- and 4( S)-fluoroproline solely from 4( R)-hydroxyproline

As building blocks of collagen model peptides, Boc- and Fmoc-protected 4( R)- and 4( S)-fluoroproline, which will be widely used in peptide synthesis including solid-phase strategy, were synthesized from the readily available 4( R)-hydroxyproline in higher yield than with conventional methods. To es...

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Bibliographic Details
Published in:	Tetrahedron Vol. 58; no. 42; pp. 8453 - 8459
Main Authors:	Doi, Masamitsu, Nishi, Yoshinori, Kiritoshi, Naruto, Iwata, Tomoya, Nago, Mika, Nakano, Hiroaki, Uchiyama, Susumu, Nakazawa, Takashi, Wakamiya, Tateaki, Kobayashi, Yuji
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 14-10-2002
Subjects:	4( R)-hydroxyproline 4-fluoroproline collagen model peptides Mitsunobu reaction stereoselective synthesis X-Ray analysis 4( R)-hydroxyproline 4-fluoroproline collagen model peptides stereoselective synthesis Mitsunobu reaction X-Ray analysis
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Summary:	As building blocks of collagen model peptides, Boc- and Fmoc-protected 4( R)- and 4( S)-fluoroproline, which will be widely used in peptide synthesis including solid-phase strategy, were synthesized from the readily available 4( R)-hydroxyproline in higher yield than with conventional methods. To establish the stereospecificity of the Mitsunobu reaction and the subsequent fluorination that were presumed to cause the inversion of configuration at the C-4 position of a proline derivative, the absolute configuration of one of the key products, Boc-4( S)-fluoroproline, was determined by X-ray crystallography. Graphic
ISSN:	0040-4020 1464-5416
DOI:	10.1016/S0040-4020(02)01020-7