racemization on Ac-Trp coupling

Richard Skubish (rskubish@pharmdec.wustl.edu)
Wed, 8 Jan 1997 11:18:29 -0600

Date: Wed, 8 Jan 1997 11:18:29 -0600
Message-Id: <v01530501aefa84da5e29@[128.252.197.88]>
To: abrfhyp@cco.caltech.edu
From: rskubish@pharmdec.wustl.edu (Richard Skubish)
Subject: racemization on Ac-Trp coupling

Can anyone tell me if I should expect racemization coupling Ac-Trp-OH to
a peptide using HOBT/TBTU activation? I did a solution coupling to a
diaminodiol central group and the resulting pseudotetrapeptide shows two
peaks in RF-HPLC (3:1) both with the correct mass. I am worried that the
absence of the urethane bond as present in Fmoc-AAcids may result in
increased racemization even if HOBT is present.

Thanks,
Alex Tossi
Dept. Biochemistry
Univ. Trieste

Richard Skubish
rskubish@pharmdec.wustl.edu
314-362-0283
Washington University Medical School
Box 8103 - PNACL
660 S. Euclid
St. Louis, MO 63110