98929-91-0Relevant academic research and scientific papers
Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
Chennakrishnareddy, Gundala,Nagendra, Govindappa,Hemantha, Hosahalli P.,Das, Ushati,Guru Row, Tayur N.,Sureshbabu, Vommina V.
supporting information; experimental part, p. 6718 - 6724 (2010/09/30)
Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The 1H NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenoureido derivatives is free from racemization.
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.
The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids
Mangette, John E.,Johnson, Matthew R.,Le, Van-Duc,Shenoy, Rajesh A.,Roark, Howard,Stier, Michael,Belliotti, Thomas,Capiris, Thomas,Guzzo, Peter R.
experimental part, p. 9536 - 9541 (2009/12/28)
Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.
Total synthesis of nosiheptide. Synthesis of thiazole fragments
Koerber-Ple,Massiot
, p. 1309 - 1315 (2007/10/03)
The preparation of three new thiazole derivatives from natural products is described, as well as improvements in the synthesis of ethyl 2-aminomethyl-4-thiazolecarboxylate.
Efficient, racemization-free amidation of protected amino acids
Somlai,Szokan,Balaspiri
, p. 285 - 287 (2007/10/02)
N-tert-Butoxycarbonyl derivatives of L-leucine, S-benzyl-L-cysteine and N(τ)-(2,4-dinitrophenyl)-L-histidine were amidated with crystalline ammonium, methylammonium, and ethylammonium salts of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one and N-hydroxy-succinimi
