We have synthesized many statine containing peptides both by Boc and Fmoc
chemistry. To save on the consumption of any expensive amino acids, in this
case the Fmoc-Statine, we do the coupling manually, using 1.5 to 2 times
excess instead of the standard 4 times excess for normal amino acids. Check
the completeness of coupling using ninhydrin test before proceeding with the
removal of the Fmoc group. Do the cleavage and deprotection using the
standard protocol. Do not acetylate the peptide, the statine will be
acetylated. If you need to acetylate the peptide thus forming acetylated
statine, you can remove the acetyl group from the statine by performing
hydrolysis using LiOH solution.
Anita Hong
AnaSpec, Inc.
2149 O'Toole Avenue, Suite F
San Jose, CA 95131
(408)452-5055 (phone)
(408)452-5059 (fax)
e-mail: service@anaspec.com
home-page: www.anaspec.com
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AnaSpec was recognized as a "Leader of the Pack"
in custom peptide synthesis by The Scientist (October 27, 1997)
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-----Original Message-----
From: Mark Lively <mlively@medcenter.wpmail.wfu.edu>
To: Recipients of ABRF List <abrf@aecom.yu.edu>
Date: Wednesday, October 21, 1998 11:21 AM
Subject: PepSyn Peptides with statine
>ABRFers,
>
>Query: Has anyone synthesized peptide containing "statine" using Fmoc
chemistry?
>
> We have been asked to synthesize a heptapeptide containing a "statine"
residue in the 5th amino acid position. Statine is
(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid:
>
>(CH3)2CH-CH2-CH(NH2)-CH(OH)-CH2-COOH
>
>The Fmoc derivative is available commercially but is quite expensive. We
will have only a single shot at making this peptide and I am concerned about
differences in the coupling chemistry. We have a literature citation (J.
Med. Chem. 31:1679, 1988) that prepared a range of peptides containing this
derivative. They used t-Boc chemistry and extended the coupling time to 10
hours for the statine derivative. Furthermore, the 3-hydroxy group was left
unprotected.
> I would appreciate any advice regarding this synthesis. We currently use
Fast-Moc chemistry (HBTU) on an ABI 430 peptide synthesizer. Specifically,
is it necessary to extend the coupling time? Second, do I need to be
concerned about the unprotected 3-hudroxy group?
>
>Thanks in advance for your help.
>
>Mark Lively
>
>Mark O. Lively, Ph.D., Professor of Biochemistry
>Molecular Genetics Program Director
>Wake Forest University School of Medicine
>Medical Center Blvd., Winston-Salem, NC 27157
>Phone: 336-716-2969 Fax: 336-716-7200
>Email: mlively@wfubmc.edu
>
>