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Chemoenzymatic Synt...
Chemoenzymatic Synthesis of O-Mannosylpeptides in Solution and on Solid Phase
- Article/chapterEnglish2012
Publisher, publication year, extent ...
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2012-03-01
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American Chemical Society (ACS),2012
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printrdacarrier
Numbers
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LIBRIS-ID:oai:DiVA.org:su-76150
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https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-76150URI
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https://doi.org/10.1021/ja211861mDOI
Supplementary language notes
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Language:English
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Summary in:English
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Subject category:ref swepub-contenttype
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Subject category:art swepub-publicationtype
Notes
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12
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O-Mannosyl glycans are known to play an important role in regulating the function of alpha-dystroglycan (alpha-DG), as defective glycosylation is associated with various phenotypes of congenital muscular dystrophy. Despite the well-established biological significance of these glycans, questions regarding their precise molecular function remain unanswered. Further biological investigation will require synthetic methods for the generation of pure samples of homogeneous glycopeptides with diverse sequences. Here we describe the first total syntheses of glycopeptides containing the tetrasaccharide NeuNAc alpha 2-3Gal beta 1-4GlcNAc beta 1-2Man alpha, which is reported to be the most abundant O-mannosyl glycan on alpha-DG. Our approach is based on biomimetic stepwise assembly from the reducing end and also gives access to the naturally occurring mono-, di-, and trisaccharide substructures. In addition to the total synthesis, we have developed a one-pot enzymatic cascade leading to the rapid synthesis of the target tetrasaccharide. Finally, solid-phase synthesis of the desired glycopeptides directly on a gold microarray platform is described.
Subject headings and genre
Added entries (persons, corporate bodies, meetings, titles ...)
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Green, Anthony P.
(author)
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Laurent, Nicolas
(author)
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Both, Peter
(author)
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Fontana, CarolinaStockholms universitet,Institutionen för organisk kemi(Swepub:su)cfont
(author)
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Voglmeir, Josef
(author)
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Weissenborn, Martin J.
(author)
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Haddoub, Rose
(author)
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Grassi, Paola
(author)
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Haslam, Stuart M.
(author)
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Widmalm, GöranStockholms universitet,Institutionen för organisk kemi(Swepub:su)gw
(author)
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Flitsch, Sabine L.
(author)
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Stockholms universitetInstitutionen för organisk kemi
(creator_code:org_t)
Related titles
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In:Journal of the American Chemical Society: American Chemical Society (ACS)134:10, s. 4521-45240002-78631520-5126
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Sardzik, Robert
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Green, Anthony P ...
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Laurent, Nicolas
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Both, Peter
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Fontana, Carolin ...
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Voglmeir, Josef
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Weissenborn, Mar ...
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Haddoub, Rose
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Grassi, Paola
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Haslam, Stuart M ...
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Widmalm, Göran
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Flitsch, Sabine ...
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Biochemistry and ...
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Journal of the A ...
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Stockholm University