Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.

Khalil, A; Ishita, K; Ali, T; Tiwari, R; Riachy, R; Toppino, A; Hasabelnaby, S; Sayfullin, N; Oliver, AG; Gallucci, J; Huang, Z; Tjarks, W

Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.

Khalil, A Ishita, K Ali, T Tiwari, R Riachy, R Toppino, A Hasabelnaby, S Sayfullin, N Oliver, AG Gallucci, J Huang, Z

Tjarks, W

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Publisher:: TAYLOR & FRANCIS INC
Publication Type:: Journal Article
Citation:: Nucleosides Nucleotides Nucleic Acids, 2014, 33, (12), pp. 786-799
Issue Date:: 2014

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Field	Value	Language
dc.contributor.author	Khalil, A
dc.contributor.author	Ishita, K
dc.contributor.author	Ali, T
dc.contributor.author	Tiwari, R
dc.contributor.author	Riachy, R
dc.contributor.author	Toppino, A
dc.contributor.author	Hasabelnaby, S
dc.contributor.author	Sayfullin, N
dc.contributor.author	Oliver, AG
dc.contributor.author	Gallucci, J
dc.contributor.author	Huang, Z https://orcid.org/0000-0003-1985-0884
dc.contributor.author	Tjarks, W
dc.date.accessioned	2024-02-19T22:55:03Z
dc.date.available	2024-02-19T22:55:03Z
dc.date.issued	2014
dc.identifier.citation	Nucleosides Nucleotides Nucleic Acids, 2014, 33, (12), pp. 786-799
dc.identifier.issn	1525-7770
dc.identifier.issn	1532-2335
dc.identifier.uri	http://hdl.handle.net/10453/175754
dc.description.abstract	The reaction of thymidine, 3-mono-, and 3,3',5'-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic-, and β-pyranosidic nucleosides. On the other hand, 3,3',5'-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.
dc.format	Print
dc.language	eng
dc.publisher	TAYLOR & FRANCIS INC
dc.relation.ispartof	Nucleosides Nucleotides Nucleic Acids
dc.relation.isbasedon	10.1080/15257770.2014.945648
dc.rights	info:eu-repo/semantics/closedAccess
dc.subject	0601 Biochemistry and Cell Biology
dc.subject.classification	Organic Chemistry
dc.subject.classification	3101 Biochemistry and cell biology
dc.subject.classification	3404 Medicinal and biomolecular chemistry
dc.subject.mesh	Chlorides
dc.subject.mesh	Glycosides
dc.subject.mesh	Hydrolysis
dc.subject.mesh	Iodides
dc.subject.mesh	Thymidine
dc.subject.mesh	Chlorides
dc.subject.mesh	Iodides
dc.subject.mesh	Glycosides
dc.subject.mesh	Thymidine
dc.subject.mesh	Hydrolysis
dc.subject.mesh	Chlorides
dc.subject.mesh	Glycosides
dc.subject.mesh	Hydrolysis
dc.subject.mesh	Iodides
dc.subject.mesh	Thymidine
dc.title	Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.
dc.type	Journal Article
utslib.citation.volume	33
utslib.location.activity	United States
utslib.for	0601 Biochemistry and Cell Biology
pubs.organisational-group	University of Technology Sydney
pubs.organisational-group	University of Technology Sydney/Faculty of Engineering and Information Technology
pubs.organisational-group	University of Technology Sydney/Faculty of Engineering and Information Technology/School of Civil and Environmental Engineering
pubs.organisational-group	University of Technology Sydney/Strength - CTWW - Centre for Technology in Water and Wastewater Treatment
pubs.organisational-group	University of Technology Sydney/Strength - CGT - Centre for Green Technology
utslib.copyright.status	closed_access	*
dc.date.updated	2024-02-19T22:55:00Z
pubs.issue	12
pubs.publication-status	Published
pubs.volume	33
utslib.citation.issue	12

Abstract:

The reaction of thymidine, 3-mono-, and 3,3',5'-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic-, and β-pyranosidic nucleosides. On the other hand, 3,3',5'-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.

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http://hdl.handle.net/10453/175754