EFFECT OF SOLVENT ON RACEMIZATION IN CARBODIIMIDE MEDIATED SOLID-PHASE FRAGMENT CONDENSATIONS

被引：9

作者：

HAVER, AC ^{[1
]}

SMITH, DD ^{[1
]}

机构：

[1] CREIGHTON UNIV,SCH MED,DEPT BIOMED SCI,2500 CALIF PLAZA,OMAHA,NE 68178

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 14期

关键词：

RACEMIZATION; SOLVENT EFFECTS; SOLID PHASE FRAGMENT CONDENSATION; DIISOPROPYLCARBODIIMIDE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

D O I：

10.1016/S0040-4039(00)77583-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH-1 was coupled to Leu-PAM resin with DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HPLC to separate the epimers. Solvents used were DMF, NMP, TFE, and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable (< 0.1%).

引用

页码：2239 / 2242

页数：4

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