Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5-methyluridine

Anu Arya; Divia  Mathur; Abhilash Tyagi; Rajesh Kumar; Vinod Kumar; Carl Erik Olsen; Rajendra K. Saxena; Ashok K. Prasad

doi:10.1080/15257770.2013.847957

Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5-methyluridine

Anu Arya, Divia Mathur, Abhilash Tyagi, Rajesh Kumar, Vinod Kumar, Carl Erik Olsen, Rajendra K. Saxena, Ashok K. Prasad

Section for Plant Biochemistry

8 Citations (Scopus)

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 K₂CO₃ in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, ¹H-, ¹³C NMR spectra, and high-resolution mass spectra) data analysis.

Original language	English
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	32
Issue number	12
Pages (from-to)	646-659
Number of pages	14
ISSN	1525-7770
DOIs	https://doi.org/10.1080/15257770.2013.847957
Publication status	Published - 1 Jan 2013

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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 K2CO3 in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.",

author = "Anu Arya and Divia Mathur and Abhilash Tyagi and Rajesh Kumar and Vinod Kumar and Olsen, {Carl Erik} and Saxena, {Rajendra K.} and Prasad, {Ashok K.}",

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doi = "10.1080/15257770.2013.847957",

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T1 - Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5-methyluridine

AU - Arya, Anu

AU - Mathur, Divia

AU - Tyagi, Abhilash

AU - Kumar, Rajesh

AU - Kumar, Vinod

AU - Olsen, Carl Erik

AU - Saxena, Rajendra K.

AU - Prasad, Ashok K.

PY - 2013/1/1

Y1 - 2013/1/1

N2 - 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 K2CO3 in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.

AB - 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 K2CO3 in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.

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DO - 10.1080/15257770.2013.847957

M3 - Journal article

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SN - 1525-7770

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EP - 659

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 12

ER -

Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5-methyluridine

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