1172596-36-9Relevant academic research and scientific papers
Synthesis of N -fmoc-protected amino alkyl thiocyanates/selenocyanates and their application in the preparation of 5-substituted S/Se -linked tetrazoles
Sureshbabu, Vommina V.,Vasantha, Basavalingappa,Hemantha, Hosahalli P.
body text, p. 1447 - 1455 (2011/06/19)
A novel class of N-Fmoc-protected amino alkyl thiocyanates/selenocyanates has been prepared by thiocyanation/selenocyanation of the corresponding alkyl iodides. These thiocyanates/selenocyanates undergo a facile [2+3]-cycloaddition reaction with sodium az
Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual utility of Poc-group for inserting carbamate-triazole units into peptide backbone
Hemantha, Hosahalli P.,Lamani, Ravi S.,Sureshbabu, Vommina V.
body text, p. 267 - 275 (2011/10/04)
Synthesis of new types of peptidomimetics and glycosylated amino acids possessing 1,2,3-triazole and carbamate moieties is described. Poc-protected amino acid esters/1-amino sugars were subjected to Cu(I) catalyzed [2+3]cycloaddition with desired azides u
N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
supporting information; experimental part, p. 5260 - 5266 (2009/12/06)
(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics
Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
body text, p. 7062 - 7066 (2010/03/01)
An efficient protocol for the synthesis of a new series of dithiocarbamate-linked peptidomimetics is described. The in situ generated dithiocarbamic acid intermediate formed by the reaction of an amino acid ester and carbon disulfide in the presence of triethylamine was treated with N-protected amino alkyl iodide to afford title compounds 3a-g in good to moderate yields. The synthesis of N-Fmoc-protected tripeptidomimetics 4a-e containing two dithiocarbamate linkages is also described. The protocol was further extended to synthesize N,N′-orthogonally protected dithiocarbamate-linked dipeptidomimetics 7a-c as well. The mild reaction conditions and non-toxic reagents are the advantages of the present method.
