Chen F M, Lee Y C, Benoiton N L
Department of Biochemistry, University of Ottawa, Ontario, Canada.
Int J Pept Protein Res. 1991 Aug;38(2):97-102. doi: 10.1111/j.1399-3011.1991.tb01416.x.
N-9-Fluorenylmethoxycarbonyl-(Fmoc) amino-acid chlorides have been prepared by reaction of hydrogen chloride on purified mixed Fmoc-amino acid-monoalkyl carbonic acid anhydrides in dichloromethane. The products partially undergo subsequent conversion to the corresponding esters due to the presence of the liberated alcohol, the extent depending on the nature of the alkyl group. Esterification occurred to 5-20% when the alkyl group was isopropyl. Anhydrides of monoisopropenyl carbonic acid which liberate acetone instead of an alcohol gave products uncontaminated with ester. The three components in a reaction mixture could be determined as the reaction progressed by normal phase high-performance liquid chromatography of aliquots, which had been freed of excess hydrogen chloride, on a mu Porasil (underivatized silica) column using tert.-butanol-hexane (1.5:98.5) as solvent.
通过在二氯甲烷中使氯化氢与纯化的混合芴甲氧羰基（Fmoc）-氨基酸-单烷基碳酸酐反应，制备了N-9-芴甲氧羰基-（Fmoc）-氨基酸氯化物。由于释放出的醇的存在，产物部分随后转化为相应的酯，转化程度取决于烷基的性质。当烷基为异丙基时，酯化反应的发生率为5-20%。释放出丙酮而非醇的单异丙烯基碳酸酐得到的产物不含酯杂质。反应混合物中的三种组分可在反应进行过程中通过对已除去过量氯化氢的等分试样进行正相高效液相色谱法测定，使用μ Porasil（未衍生化硅胶）柱，以叔丁醇-己烷（1.5:98.5）作为溶剂。
