79839-25-1Relevant academic research and scientific papers
Protected Lactam-Bridged Dipeptides for Use as Conformational Constraints in Peptides
Freidinger, Roger M.,Perlow, Debra Schwenk,Veber, Daniel F.
, p. 104 - 109 (2007/10/02)
General methods have been devised for the synthesis of lactam-constrained dipeptide analogues having five-, six-, and seven-membered rings.Three different paths from protected chiral α-amino acids to lactams involving intramolecular alkylation, intramolecular acylation, and insertion of a one carbon unit by condensation with formaldehyde have been utilized.The first two methods produce chiral products stereospecifically, but considerable racemization occurs in the third route which leads to a 4-oxo-5-amino-1,3-thiazine (13).The products are prepared in good yield and have protecting groups making them suitable for incorporation into higher peptides by methods commonly used.
