Date: Wed, 8 Jan 1997 06:33:25 -0600 (CST)
From: George Barany <barany@maroon.tc.umn.edu>
Subject: Re: PepSyn
In-Reply-To: <Pine.PMDF.3.91.970107133842.538968428A-100000@mgrp.bgsm.edu>
To: Recipients of ABRF List <abrf@aecom.yu.edu>
Mark, this sort of stuff is real easy to do. don't use Meb, though, i
don't think it will come off under the conditions that remove the
side-chain protecting groups of Fmoc chemistry. i think that Trt
derivative of Mpa is commercially available, maybe from Peptides
International but i'm not sure. We've used Mpa(Tmob) and Mpa(Xan) which
we make ourselves. Reference to Mpa(Tmob) = Mark C. Munson, Michal Lebl,
Jirina Slaninova, and George Barany. Solid-Phase Synthesis and Biological
Activity of the Parallel Dimer of Deamino-Oxytocin. Peptide Research 6,
155-159 (1993). Lin Chen is a student in my lab who has just submitted
his Ph.D. thesis, and has a lot of experience in this area. Let me know
if you need any more details. GB
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
George Barany Telephone: (612) 625-1028
Professor of Chemistry,
Laboratory Medicine & Pathology
Department of Chemistry FAX: (612) 626-7541
University of Minnesota e-mail: barany@maroon.tc.umn.edu
207 Pleasant St. S.E.
Minneapolis, MN 55455
On Tue, 7 Jan 1997, Mark Lively wrote:
> Two questions for the peptide chemists in the audience.
>
> 1. We wish to make a short peptide (7 residues) that contains an
> N-terminal (3-thio)propionic acid residue. It will look like an
> N-terminal Cys without its amino group. Using FastMoc chemistry on an ABI
> 430 synthesizer, I propose to add the thiopropionyl "residue" as its
> 4-methyl-benzyl-3-thio propionic acid derivative coupled using a normal
> amino acid coupling cycle. Assuming this coupling should work, will the
> 4-methyl-benzyl protecting group be removed by TFA using typical FMOC
> deprotection cocktails? This group has been used in t-Boc chemistry to
> make peptides containing this group and is apparently readily removed
> using HF. Alternatively, we could potentially use Trityl-thio-propionate,
> the analog of Trityl-Cys that we currently use for our Cys derivatives
> but this would require obtaining Trityl-3-thio-propionic acid.
>
> 2. Does anyone know of a source for Fmoc-homoarginine(Pmc)-OH?
> (Pmc = pentamethylchroman-6-sulphonyl)
>
> Many thanks in advance and New Year's greetings to all, especially the
> "small angel" at the helm of this cyber ship.
> \ml
>
> ------------------------------------------------------------------------------
> Mark O. Lively, Ph.D. Voice: 910-716-2969
> Professor of Biochemistry Fax: 910-716-7671
> Bowman Gray School of Medicine email: Lively@mgrp.bgsm.edu
> Wake Forest University
> Winston-Salem, NC 27157
> Home page: http://www.bgsm.edu/molecular_genetics/
> -------------------------------------------------------------------------------
>