“ Thioureidopeptide”: Novel Synthon for the Synthesis of N, N′, N″-Trisubstituted Guanidinopeptide Mimics

The synthesis of N α-protected N,N′,N″-trisubstituted guanidinopeptide mimic molecules suitably decorated in peptide backbone has been delineated in one pot employing HgCl2 as a desulphurizing agent. Chiral N α -protected thioureidopeptide esters were employed as synthons for the synthesis of title molecules. The protocol is simple and the reaction conditions employed were mild, amenable to the amino acid chemistry

A Unified Approach to Access N-Acyl Sulfonamide Tethered Peptide Conjugates

Herein we demonstrate a chemoselective reaction of Nβ-protected amino alkyl sulfonyl azides with in situ generated Nα-protected amino acid selenocarboxylates via step wise intramolecular cyclization followed by decomposition to obtain N-acyl sulfonamide tethered peptidyl conjugates. The protocol offers the synthesis of orthogonally protected N-acyl sulfonamide tethered peptidomimetics under simple and mild reaction conditions employing commercially available amino acids in presence of NaBH2Se3 as a selenating agent. Also, the synthesis of N-acyl sulfonamide tethered amino acid and aryl conjugates were accomplished as an extension of the above strateg

A Simple, Mild and Straight forward Route for the Synthesis of α-Ureidopeptidomimetics Using Cbz-Protected Amino Acid Esters

The synthesis of α-ureidopeptidomimetics employing a simple, mild and straight forward route starting from benzyloxy carbonyl (Cbz-) protected amino acid esters in presence of 2-Cl pyridine (2-chloropyridine) and Tf2O (triflic anhydride) in one-pot is described. The in situ generated isocyanate intermediates react with amino acid esters to yield the title compounds in good yields (89-96%) and the protocol proved to be racemization free

Synthesis of N-Urethane Protected Amino Alkyl (S-methyl)-Isothiouronium Compounds and Carbodiimide Tethered Peptidomimetics: An Application for Guanidino and Substituted Guanidino Peptidomimetics Synthesis

The synthesis of N,N′-disubstituted and N,N′,N′′-trisubstituted guanidine linked peptidomimetic molecules suitably decorated in the peptide backbone has been delineated. Nα-Protected amino acid derived S-methyl isothiouronium derivatives are employed as the key intermediates for the synthesis of guanidinopeptide mimics. Synthesis of a new class of carbodiimide tethered dipeptidomimetics has also been outlined wherein a Staudinger-aza-Wittig type reaction between amino alkyl azide and isothiocyanato esters is employed. Thus obtained carbodiimides have been demonstrated as starting materials for the construction of guanidino peptide mimics as well as an array of trisubstituted guanidine mimetics bearing N-hydroxy, cyano and amino function as third substitutions at the guanidino unit in the backbone