Partially modified retro‐inverso peptides

• Published in: International Journal of Peptide and Protein Research
• Main Authors: CHOREV, MICHAEL, GOODMAN, MURRAY
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1983
• Subjects: Carbonic acid
• Online Access: http://dx.doi.org/10.1111/j.1399-3011.1983.tb03103.x; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1399-3011.1983.tb03103.x; https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1983.tb03103.x

Several synthetic routes are reported to prepare the hetero diprotected 1,1‐diaminoalkanes from N ‐acylated amino acids or peptides for incorporation into partially modified retro‐inverso peptides. The Curtius rearrangement was carried out on the N ‐protected aminoacyl azides obtained from the N ‐protected aminoacyl hydrazide by nitrosyl chloride or by sodium azide reaction with an appropriate mixed carboxylic carbonic acid anhydride. The resulting isocyanate was allowed to react with alcohol to give a urethane‐type protecting group or, via a “one‐pot” approach, directly with a carboxyl carrying component to yield the modified (reversed) peptide bond. The carboxyl component can be either an N ‐acylated amino acid or a malonic acid. The more standard route involves selective deprotection of the 1,1‐diaminoalkane residue followed immediately by coupling with a carboxyl component to yield the same modified peptide derivative.