Rao P N, Burdett J E, Cessac J W, DiNunno C M, Peterson D M, Kim H K
Int J Pept Protein Res. 1987 Jan;29(1):118-25. doi: 10.1111/j.1399-3011.1987.tb02237.x.
The DL-arylamino acid ethyl ester derivatives of beta-(3-pyridyl)-DL-alanine, and beta-(3-benzo[b]thienyl)-DL-alanine were synthesized by diethyl acetamidomalonate condensation with the respective arylmethyl halides followed by partial hydrolysis to the monoethyl ester and decarboxylation. Each derivative was enzymatically resolved to a separable mixture of the corresponding N-acetyl-L-amino acid and the unchanged D amino acid derivative. Acidic hydrolysis of the latter gave the corresponding D-amino acid, the optical purity of which was established by HPLC analysis of the 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) derivative. The free D amino acids were converted to D-BOC derivatives by reaction with di-tert-butyldicarbonate in tert-butyl alcohol, water and sodium hydroxide.
通过乙酰氨基丙二酸二乙酯与相应的芳基甲基卤化物缩合，然后部分水解为单乙酯并脱羧，合成了β-(3-吡啶基)-DL-丙氨酸和β-(3-苯并[b]噻吩基)-DL-丙氨酸的DL-芳基氨基酸乙酯衍生物。每种衍生物通过酶法拆分为相应的N-乙酰-L-氨基酸和未变化的D-氨基酸衍生物的可分离混合物。后者的酸性水解得到相应的D-氨基酸，其光学纯度通过对2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯（GITC）衍生物的HPLC分析确定。游离的D-氨基酸通过在叔丁醇、水和氢氧化钠中与二叔丁基二碳酸酯反应转化为D-BOC衍生物。
