关于与使用六氟磷酸苯并三唑-1-基-三（二甲氨基）鏻（BOP）相关的外消旋化研究。
Studies on racemization associated with the use of benzotriazol-1-yl-tris (dimethylamino)phosphonium hexafluorophosphate (BOP).
作者信息
Steinauer R, Chen F M, Benoiton N L
机构信息
Department of Biochemistry, University of Ottawa, Ontario, Canada.
出版信息
Int J Pept Protein Res. 1989 Oct;34(4):295-8. doi: 10.1111/j.1399-3011.1989.tb01577.x.
The influence of the amount and nature of the necessary tertiary amine on racemization attending the BOP-mediated coupling of N-benzyloxycarbonylglycyl-dipeptides has been examined by determining the epimeric products by high-performance liquid chromatography. Racemization was encountered in all cases examined that included dichloromethane as solvent. The least racemization occurred when the base was diisopropylethylamine, the most when the base was N-methylmorpholine. Excess base promoted racemization. Racemization was significantly diminished but not eliminated when 1-hydroxybenzotriazole was added to the reaction mixtures. The above results pertain to the coupling of peptide segments; they do not pertain to the coupling of N-alkoxycarbonylamino acids.
通过高效液相色谱法测定差向异构产物，研究了必要的叔胺的量和性质对BOP介导的N-苄氧羰基甘氨酰二肽偶联过程中消旋化的影响。在所考察的所有以二氯甲烷为溶剂的情况下均出现了消旋化现象。当碱为二异丙基乙胺时消旋化程度最低，当碱为N-甲基吗啉时消旋化程度最高。过量的碱会促进消旋化。当向反应混合物中加入1-羟基苯并三唑时，消旋化显著减少但并未消除。上述结果适用于肽段的偶联；不适用于N-烷氧羰基氨基酸的偶联。
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