Date: Fri, 31 Jan 1997 08:15:48 -0600 (CST)
From: Lynn Mayfield <lynnm@chop.swmed.edu>
Subject: Peptide aldehydes
To: Recipients of ABRF List <abrf@aecom.yu.edu>
Our lab is trying to put together some C terminal Arginine aldehyde
peptides by Fmoc solid phase chemistry, using 3-N-Boc-N-methoxyamino)
propionyl-B-Ala-4-methy benzhydryl amine resin from BACHEM. . We obtained
the procedure from Tetrahedron Letters Vol. 36, pp 7871-7874. The
synthesis itself went very well, but we were unable to confirm sequence of
the aldehyde structure by Mass Spec or NMR after cleavage. The method
calls for a reduction with LAH. We feel something is going wrong during
this step. Has anyone tried this method with good success, and if so
could you share your expertice with us? There may be something we are
missing. Anyone with any experience making C terminal aldehydes by other
methodology, please share also. Thanks all.