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

Authors
FIELDS CG FIELDS GB
Citation
Cg. Fields et Gb. Fields, MINIMIZATION OF TRYPTOPHAN ALKYLATION FOLLOWING 9-FLUORENYLMETHOXYCARBONYL SOLID-PHASE PEPTIDE-SYNTHESIS, Tetrahedron letters, 34(42), 1993, pp. 6661-6664
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
42
Year of publication
1993
Pages
6661 - 6664
Database
ISI
SICI code
0040-4039(1993)34:42<6661:MOTAF9>2.0.ZU;2-I
Abstract
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 protecti ng group ''scavenger'' use following Fmoc-based solid-phase synthesis. The extent of Trp alkylation was characterized and quantitated by ana lytical RP-HPLC, Edman degradation sequence analysis, and ESMS. The Pb f group offered lower TFA-induced Trp alkylation than the Pmc group. T he combination of Trp(Boc) and Arg(Pbf) resulted in extremely low leve ls of Trp alkylation during TFA treatment of the peptide-resin in the absence of scavengers.