Subject: pKa of reduced amide bond N

From: [email-masked]
Date: Sat, 04 Mar 1995 08:31:38 -0600 (CST)

I am modeling peptide mimetics which include a reduced peptide
bond.  The isosteric (CH2NH) sp3 N may be protonated under tested
biological conditions.  I was wondering if anyone can help me
with a pKa value either theoretical or experimental for this type
of nitrogen.  A pKa value for protonated dimethyl ammonium NH2+(CH3)2
would suffice as an approximation.  Thanks in advance for any help.
 
John S. Tokarski
Laboratory of Molecular Modeling and Design
College of Pharmacy
Univ. of Illinois at Chicago
833 S. Wood St., m/c 781, #539
Chicago, Il 60612
 
(312)996-6004
e-mail: [email-masked]
fax: (312) 996-7107