Activation of N,N-bis(alkoxycarbonyl) amino acids. Synthesis of N-alkoxycarbonyl amino acid N-carboxyanhydrides and N,N-dialkoxycarbonyl amino acid fluorides, and the behavior of these amino acid derivatives.
作者:Jaroslav Šavrda、Lyubov Chertanova、Michel Wakselman
DOI:10.1016/s0040-4020(01)80689-x
日期:1994.5
Series of Boc- and Cbz-NCAs (2), and of N,N-bis(alkoxycarbonyl) amino acid fluorides U2AAFs (3) have been prepared by activation of N,N-bis-Boc- and N-Cbz,N-Boc-α-amino acids (1) with the Vilsmeier reagent or cyanuric fluoride. The absence of epimerization of 2 and 3 during both their formation and their coupling under standard conditions of peptide synthesis had been demonstrated by optical purity
通过活化N,N-双-Boc-和N-Cbz,制备了一系列Boc-和Cbz-NCA(2)以及N,N-双(烷氧基羰基)氨基酸氟化物U 2 AAF(3), N-Boc-α-氨基酸(1)与Vilsmeier试剂或氰尿酰氟一起使用。通过光学纯度杨氏试验证明了在肽合成的标准条件下2和3在形成和偶联过程中没有差向异构化2和3。在双氨基甲酸酯保护的活化氨基酸的其他活化衍生物中,Boc 2 Phe-OSu的显着外消旋化表明了α-H的可交换性(8)在碱的存在下,并且由二肽Boc 2 Phe-Leu-OBn形成Dakin-West型产物11。