The aspartimide problem in Fmoc‐based SPPS. Part I
作者:
M. Mergler,
F. Dick,
B. Sax,
P. Weiler,
T. Vorherr,
期刊:
Journal of Peptide Science
(WILEY Available online 2003)
卷期:
Volume 9,
issue 1
页码: 36-46
ISSN:1075-2617
年代: 2003
DOI:10.1002/psc.430
出版商: John Wiley&Sons, Ltd.
关键词: aspartimide formation;Fmoc‐solid phase peptide synthesis;Asp β‐carboxy protection;backbone protection;Asp‐Gly motif;carboxy protection by orthoester formation
数据来源: WILEY
摘要:
AbstractA variety of Asp β‐carboxy protecting groups, Hmb backbone protection and a range of Fmoc cleavage protocols have been employed in syntheses of the model hexapeptide H‐VKDGYI‐OH to investigate the aspartimide problem in more detail. The extent of formation of aspartimide and aspartimide‐related by‐products was determined by RP‐HPLC. This study included three new Fmoc‐Asp‐OH derivatives: the β‐(4‐pyridyl‐diphenylmethyl) and β‐(9‐phenyl‐fluoren‐9‐yl) esters and also the orthoester Fmoc‐β‐(4‐methyl‐2,6,7‐trioxabicyclo[2.2.2]‐oct‐1‐yl)‐alanine. 3‐Methylpent‐3‐yl protection of the Asp side chain resulted in significant improvements with respect to aspartimide formation. Complete suppression was achieved using the combination OtBu side chain protection and Hmb backbone protection for the preceding Gly residue. Copyrig
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