MINIMIZATION OF TRYPTOPHAN ALKYLATION FOLLOWING 9-FLUORENYLMETHOXYCARBONYL SOLID-PHASE PEPTIDE-SYNTHESIS

被引：63

作者：

FIELDS, CG

FIELDS, GB

机构：

[1] UNIV MINNESOTA,DEPT LAB MED & PATHOL,BOX 107,420 DELAWARE ST SE,MINNEAPOLIS,MN 55455

[2] UNIV MINNESOTA,DEPT BIOCHEM,MINNEAPOLIS,MN 55455

[3] UNIV MINNESOTA,CTR BIOMED ENGN,MINNEAPOLIS,MN 55455

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)61669-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have examined Pmc and Pbf side-chain protection of Arg and Boc side-chain protection of Trp in an attempt to minimize side-chain protecting group ''scavenger'' use following Fmoc-based solid-phase synthesis. The extent of Trp alkylation was characterized and quantitated by analytical RP-HPLC, Edman degradation sequence analysis, and ESMS. The Pbf group offered lower TFA-induced Trp alkylation than the Pmc group. The combination of Trp(Boc) and Arg(Pbf) resulted in extremely low levels of Trp alkylation during TFA treatment of the peptide-resin in the absence of scavengers.

引用

页码：6661 / 6664

页数：4

共 21 条

[1] PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].