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