Date: Wed, 22 Jan 1997 09:43:46 -0600
Message-Id: <v0153050baf0ce3c49d2a@[128.252.197.88]>
To: abrfhyp@cco.caltech.edu
From: rskubish@pharmdec.wustl.edu (Richard Skubish)
Subject: N-terminal (3-thio)propionic acid
>Date: Wed, 8 Jan 1997 06:33:25 -0600 (CST)
>From: George Barany <barany@maroon.tc.umn.edu>
>Old-To: Mark Lively <lively@mgrp.bgsm.edu>
>Cc: Recipients of ABRF List <abrf@aecom.yu.edu>,
> Lin Chen <linchen@chemsun.chem.umn.edu>
>Subject: Re: PepSyn
>Mime-Version: 1.0
>To: Recipients of ABRF List <abrf@aecom.yu.edu>
>Sender: Association of Biomolecular Resource Facilities
><abrf-request@aecom.yu.edu>
>Precedence: bulk
>
>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/
>>
>>--------------------------------------------------------------------------
>>-----
>>
>
Richard Skubish
rskubish@pharmdec.wustl.edu
314-362-0283
Washington University Medical School
Box 8103 - PNACL
660 S. Euclid
St. Louis, MO 63110