title: Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5-methyluridine.
abstract: An efficient protocol has been developed for the synthesis of a small library of 3'-deoxy-3'-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3'-azido-3'-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3'-azido-3'-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K2CO3in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, (1)H-, (13)C NMR spectra, and high-resolution mass spectra) data analysis.
authors: a Bioorganic Laboratory, Department of Chemistry , University of Delhi , Delhi , India.
authors: Anu
authors: A
authors: Arya
authors: Divya
authors: D
authors: Mathur
authors: Abhilash
authors: A
authors: Tyagi
authors: Rajesh
authors: R
authors: Kumar
authors: Vinod
authors: V
authors: Kumar
authors: Carl E
authors: CE
authors: Olsen
authors: Rajendra K
authors: RK
authors: Saxena
authors: Ashok K
authors: AK
authors: Prasad
mesh_terms: D000215:Acylation; D000818:Animals; D002175:Candida / Q000201:enzymology; D057930:Click Chemistry; D008049:Lipase / Q000378:metabolism; D013552:Swine; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism
chemical_list: D014230:Triazoles; C009182:ribothymidine; D008049:Lipase; D014529:Uridine