6832-16-2Relevant articles and documents
INVESTIGATION OF THE STAUDINGER REACTION BETWEEN BICYCLIC PHOSPHITE AND DIAZO COMPOUNDS
Pei, Chengxin,Xu, Xuanlong
, p. 143 - 148 (2007/10/02)
Nine bicyclic phosphatazines were synthesized by the Staudinger reaction between bicyclic phosphite (1) and diazo compounds (2-5), the Elemental Analysis data, IR, 31P NMR and Mass Spectral data of these compounds are reported.The reaction of diazoacetate with bicyclic phosphite was followed by 31P NMR, the concentration-time curve was simulated by Optimal Approximation with a computer.It was found that this reaction consisted of two steps, the first step was second-order and the second was first-order.A possible mechanism is also proposed.Key words: Staudingerreaction; bicyclic phosphite; phosphatazine; optimal approximation; NMR; IR.
NITROSATION OF PEPTIDE BONDS. CLEAVAGE OF NITROSATED PEPTIDES BY PYRROLIDINE AND α-AMINO ESTERS
Garcia, Jordi,Gonzalez, Javier,Segura, Ramon,Vilarrasa, Jaume
, p. 3121 - 3128 (2007/10/02)
The reaction of several α-amino acids and peptides (containing Gly, L-Ala, L-Leu, L- or DL-Phe, and/or L- or D-Val) with air-diluted nitrogen oxides has been studied to roughly mimic the N-nitrosation of peptide bonds that the contaminated urban air might produce in pulmonary tissues. Most N-protected α-amino acids give practically quantitative yields of N-nitroso derivatives. N-Protected dipeptides afford either dinitrosated peptides, mixtures of di- and mononitrosated compounds, selectively mononitrosated products, or no reaction at all, depending mainly on steric effects. The same trends are observed for some higher peptides.The (poly)nitrosated peptides, which retain the chirality of the starting materials, have been characterized by 1H and 13C NMR spectroscopy and are cleaved by pyrrolidine and amino esters under mild conditions to give (new) amides or peptides plus diazo derivatives.
