Enantiopure N-protected α-amino glyoxals 1. Synthesis from α-amino acids and some condensation reactions with amines
作者:Paul Darkins、Michelle Groarke、M. Anthony McKervey、Hazel M. Moncrieff、Noreen McCarthy、Mark Nieuwenhuyzen
DOI:10.1039/a907948c
日期:——
N-protected α-amino diazoketones has been prepared from L-amino acids and dipeptides and used as precursors in the synthesis of novel N-protected α-amino glyoxals via oxidation with distilled dimethyldioxirane (DMD) in acetone. The glyoxals have been converted, without purification, into enantiopure imines, pyrazines, quinoxalines, and pyrido[2,3-b]pyrazines via condensation with the appropriate amine or
由L-氨基酸制备了一系列N-保护的α-氨基重氮酮。二肽并用作新颖的合成的前体Ñ -保护的α氨基乙二醛经由 氧化作用 与蒸馏的二甲基二环氧乙烷(DMD) 丙酮。乙二醛已经转化,没有纯化,变成对映体 亚胺, 吡嗪,喹喔啉和吡啶并[2,3- b ]吡嗪通过与适当的缩合反应胺 或者 二胺。吡啶并[2,3- b ]吡嗪的分子结构N -Cbz- L-苯丙氨酸 由...决定 X射线分析。
Phenyl esters of N-terminal amino-protected peptides are valuable intermediates in synthesis of polypeptides. The phenyl ester function is stable during the customary manipulations of chain extension, and it can be removed selectively by treatment with one equivalent of hydrogen peroxide at pH 10.5 in a variety of solvents such as 80% acetone, dimethylfonnamide, hexamethylphosphoramide or trifluoroethanol