Racemization studies of Fmoc-Ser(tBu)-OH during stepwise continuous-flow solid-phase peptide synthesis

被引：34

作者：

Di Fenza, A ^{[1
]}

Tancredi, M ^{[1
]}

Galoppini, C ^{[1
]}

Rovero, P ^{[1
]}

机构：

[1] CNR, Ist Mutagenesi & Differenziamento, Lab Sintesi Peptid, I-56124 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

关键词：

amino acids and derivatives; racemization; solid-phase synthesis;

D O I：

10.1016/S0040-4039(98)01891-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We observed unexpectedly high levels of racemization of Fmoc-Ser(tBu)-OH during automated stepwise solid-phase peptide synthesis under standard continuous-flow conditions. We set up a model assay, based on the solid-phase assembly of the tripeptide H-Gly-Ser-Phe-NH2, in order to test the effect of the coupling conditions on serine racemization. Protocols based on collidine as the tertiary base added to the coupling reagent enabled incorporation of serine with less than 1% racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8529 / 8532

页数：4

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