Racemization in stepwise solid-phase peptide synthesis at elevated temperatures
Racemization in stepwise solid-phase peptide synthesis at elevated temperatures
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DOI：
10.1016/j.tet.2004.03.070
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发表时间：
2004-05-17
期刊：
影响因子：
2.1
通讯作者：
Miranda, MTM
中科院分区：
文献类型：
--
作者：
Souza, MP;Tavares, MFM;Miranda, MTM
The present work is an attempt to assess racemization in stepwise solid-phase peptide synthesis at elevated temperatures (SPPS-ET), a high-speed approach in which peptide elongation occurs at 55-75 degreesC. This attempt was based on the notion that a high propensity for this side reaction would hamper employment of this alternative approach and would dampen interest in its further development. Simple peptide models were synthesized using customized protocols for classical SPPS or SPPS-ET. Systematic analyses of the resulting crude peptides by reversed-phase HPLC, ion-exchange HPLC, capillary electrophoresis and electrospray ionization mass spectrometry revealed low diastereomeric byproduct contents. These results indicate that, from the standpoint of racemization, classical SPPS and SPPS-ET protocols were equivalent. Therefore, further studies employing SPPS-ET protocols are justified. (C) 2004 Elsevier Ltd. All rights reserved.
