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Naphthyl Thio- and ...
Naphthyl Thio- and Carba-xylopyranosides for Exploration of the Active Site of ß-1,4-Galactosyltransferase 7 (ß4GalT7)
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- Thorsheim, Karin (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Willén, Daniel (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Tykesson, Emil (author)
- Lund University,Lunds universitet,Matrixbiologi,Forskargrupper vid Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Matrix Biology,Lund University Research Groups,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Ståhle, Jonas (author)
- Stockholm University,Stockholms universitet,Institutionen för organisk kemi
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- Praly, Jean-Pierre (author)
- Claude Bernard University Lyon 1
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- Vidal, Sebastien (author)
- Claude Bernard University Lyon 1
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- Johnson, Magnus T. (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Widmalm, Göran (author)
- Stockholm University,Stockholms universitet,Institutionen för organisk kemi
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- Manner, Sophie (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Ellervik, Ulf (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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(creator_code:org_t)
- 2017-11-27
- 2017
- English.
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In: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 23:71, s. 18057-18065
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Abstract
Subject headings
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- Xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon were investigated as substrates for -1,4-galactosyltransferase7 (4GalT7), a key enzyme in the biosynthesis of glycosaminoglycan chains. The analogues with an endocyclic sulfur atom proved to be excellent substrates for 4GalT7, and were galactosylated approximately fifteen times more efficiently than the corresponding xyloside. The 5a-carba--xylopyranoside in the d-configuration proved to be a good substrate for 4GalT7, whereas the enantiomer in the l-configuration showed no activity. Further investigations by X-ray crystallography, NMR spectroscopy, and molecular modeling provided a rationale for the pronounced activity of the sulfur analogues. Favorable - interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme were observed for the thio analogues, which open up for the design of efficient GAG primers and inhibitors.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- carbohydrates
- enzymes
- structure-activity relationships
- xylosides
- carbohydrates
- enzymes
- structure–activity relationships
- xylosides
Publication and Content Type
- ref (subject category)
- art (subject category)
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To the university's database
- By the author/editor
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Thorsheim, Karin
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Willén, Daniel
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Tykesson, Emil
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Ståhle, Jonas
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Praly, Jean-Pier ...
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Vidal, Sebastien
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show more...
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Johnson, Magnus ...
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Widmalm, Göran
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Manner, Sophie
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Ellervik, Ulf
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
- Articles in the publication
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Chemistry - A Eu ...
- By the university
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Stockholm University
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Lund University