化学
试剂
产量(工程)
脱质子化
组合化学
肽
丙氨酸
肽合成
氨基酸
有机化学
立体化学
生物化学
离子
材料科学
冶金
作者
Markus Obkircher,Christian Stähelin,Fritz Dick
摘要
Abstract During the Fmoc‐protection of H–α‐Me–Val–OH, an unknown side product was found and isolated. The characterization using various analytical methods led unambiguously to the result that Fmoc–β‐Ala–OH was formed during the reaction. The reagent Fmoc–OSu was proven to be the source of Fmoc–β‐Ala–OH, following a mechanism that involved many deprotonation and elimination steps and a Lossen‐type rearrangement as key sequence. The impurity Fmoc–β‐Ala‐OH was found in a variety of reactions in which Fmoc–OSu was applied, either in the reaction mixture or as a contamination of the crude product. Purification of the Fmoc–amino acid derivatives from this impurity incurred high costs and significant reductions in yield. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.
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