60336-71-2Relevant academic research and scientific papers
Stereoselective formation of a functionalized dipeptide isostere by zinc carbenoid-mediated chain extension
Lin, Weimin,Theberge, Cory R.,Henderson, Timothy J.,Zercher, Charles K.,Jasinski, Jerry,Butcher, Ray J.
supporting information; experimental part, p. 645 - 651 (2009/07/04)
The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-exten
The hydrolysis of primary amide groups in Asn/Gln-containing peptides
Onoprienko,Yelin,Miroshnikov
, p. 361 - 368 (2007/10/03)
Peptides Boc-Ala-Asn/Gln-OH and Boc-Asn/Gln-Ala-OH were saponified with barium hydroxide to corresponding Asp/Glu-containing peptides. Under the conditions of saponification, Boc-Asn-Ala-OH additionally afforded Boc-Asp-OH, isopeptide Boc-Asp(Ala)-OH, and Boc-NHSuc > Ala-OH, with the third being the key intermediate in these transformations. Boc-Asp(OMe)-Ala-OMe underwent similar transformations under treatment with diazomethane or triethylamine. Saponification with barium hydroxide was accompanied by a high epimerization of N-terminal amino acid residues, whereas the products of the diazomethane treatment of Boc-Asp(OMe)-Ala-OMe had a low degree of epimerization.
