Simple and efficient syntheses of Boc- and Fmoc-protected 4(R)- and 4(S)-fluoroproline solely from 4(R)-hydroxyproline
Simple and efficient syntheses of Boc- and Fmoc-protected 4(R)- and 4(S)-fluoroproline solely from 4(R)-hydroxyproline
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DOI：
10.1016/s0040-4020(02)01020-7
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发表时间：
2002-10-14
期刊：
影响因子：
2.1
通讯作者：
Kobayashi, Y
中科院分区：
文献类型：
--
作者：
Doi, M;Nishi, Y;Kobayashi, Y
Boc-和fmoc保护的4(R)-和4(S)-氟脯氨酸作为胶原模型肽的组成部分，将广泛应用于包括固相策略在内的肽合成中，并以比传统方法更高的收率从现成的4(R)-羟脯氨酸中合成。Mitsunobu反应和随后的氟化反应被认为会导致脯氨酸衍生物C-4位置的构型反转，为了确定其立体特异性，用x射线晶体学确定了关键产物之一Boc-4(S)-氟脯氨酸的绝对构型。(C) 2002 Elsevier Science Ltd.版权所有。
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 stereo specificity 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. (C) 2002 Elsevier Science Ltd. All rights reserved.