Date: Wed, 22 Jan 1997 09:44:14 -0600
Message-Id: <v0153050caf0ce3e5a4e8@[128.252.197.88]>
To: abrfhyp@cco.caltech.edu
From: rskubish@pharmdec.wustl.edu (Richard Skubish)
Subject: N-terminal (3-thio)propionic acid
>Comments: Authenticated sender is <titov@ibch.siobc.ras.ru>
>From: "Vladimir Titov" <titov@ibch.wustl.edu>
>Organization: Shemyakin-Ovchinnikov Institute of bioorgan
>Old-To: Mark Lively <lively@mgrp.bgsm.edu>
>Date: Wed, 8 Jan 1997 15:44:23 +0300
>Mime-Version: 1.0
>Subject: Re: PepSyn
>Cc: abrf@aecom.yu.edu
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>To: Recipients of ABRF List <abrf@aecom.yu.edu>
>Sender: Association of Biomolecular Resource Facilities
><abrf-request@aecom.yu.edu>
>Precedence: bulk
>
>> 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.
>
>The MBzl group is stable towards TFA. Consider to use HF cleavage or Trt
>or Acm protection
>
>
>
>Vladimir Titov
>
>MailTo:titov@ibch.siobc.ras.ru
>http://titov.siobc.ras.ru
>
Richard Skubish
rskubish@pharmdec.wustl.edu
314-362-0283
Washington University Medical School
Box 8103 - PNACL
660 S. Euclid
St. Louis, MO 63110