Date: Mon, 3 Feb 97 09:19:05 CST
Message-Id: <9702031519.AA12699@audumla>
From: jsmcmur@audumla.mdacc.tmc.edu (John S. McMurray)
Subject: Re: References on Cyclic Peptides
To: Recipients of ABRF List <abrf@aecom.yu.edu>
>
>Dear ABRF's:
>
>Could somebody please provide me some basic references on cyclic peptides
>and combinatorial libraries.
>I'm being restructured !
>
>Thanks.
>
>C. Patrick McAtee, Ph.D.
>Genelabs Technologies, Inc.>
Patrick,
We have done a fair amount of work on the synthesis of cyclic peptides using
both solid-phase synthesis/solution-phase cyclization procedures and
solid-phase procedures involving side-chain attachment to the support as
well as on-resin cyclization. Our large decapeptides were not amenable to
solid-phase cyclization because of racemization and oligomerization.
However, Arno Spatola has been quite successful in generating libraries of
cyclic heptamers, hexamers and pentamers using on-resin cyclization. Note
these are cyclized in the "head-to-tail" manner. The references below may
be helpful. Our Peptide Research article has a general overview of on-resin
cyclization techniques.
Spatola, A.F., Darlak, K. and Romanovskis, P. "An approach to cyclic peptide
libraries: Reducing epimerization in medium sized rings during solid phase
synthesis" Tetrahedron Letters 37:591-594, 1996.
McMurray, J. S. Solid phase synthesis of a cyclic peptide using Fmoc
chemistry. Tetrahedron Letters 32:7679-7682, 1991.
McMurray, J.S., Budde, R.J.A., and Dyckes, D.F. Cyclic peptide substrates
of pp60c-src. Synthesis and evaluation. Int. Journal of Peptide & Protein
Research 42:209-215, 1993.
McMurray, J.S., and Lewis, C.A. The synthesis of cyclic peptides using Fmoc
solid-phase chemistry and the linkage agent
4-hydroxymethyl-3-methoxyphenoxybutyric acid. Tetrahedron Letters,
34:8059-8062, 1993.
McMurray, J.S., Lewis, C.A. and Obeyesekere, N.U. The influence of solid
support, solvent, and coupling reagent on the head-to-tail cyclization of
resin bound peptides. Peptide Research 7:195-206, 1994.
Good luck,
John
John S. McMurray
University of Texas M.D. Anderson Cancer Center
Department of Neuro-Oncology, Box 316
1515 Holcombe Blvd.
Houston, TX 77030
Phone: 713-745-3763
Fax: 713-745-1183
jsmcmur@utmdacc.uth.tmc.edu