Synthesis of a Dimer of β-(1,4)-l-Arabinosyl-(2S,4R)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort

Nα-tert-Butoxycarbonyl-l-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-l-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively t...

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Published in:Organic letters 2010-11, Vol.12 (21), p.4968-4971
Main Authors: Xie, Ning, Taylor, Carol M
Format: Article
Language:English
Subjects:
Allergens - chemistry
Antigens, Plant - chemistry
Artemisia - chemistry
Dimerization
Glycosylation
Molecular Structure
Plant Proteins - chemistry
Proline - analogs & derivatives
Proline - chemical synthesis
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description Nα-tert-Butoxycarbonyl-l-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-l-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.
doi_str_mv 10.1021/ol102112z
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Allergens - chemistry
Antigens, Plant - chemistry
Artemisia - chemistry
Dimerization
Glycosylation
Molecular Structure
Plant Proteins - chemistry
Proline - analogs & derivatives
Proline - chemical synthesis
title Synthesis of a Dimer of β-(1,4)-l-Arabinosyl-(2S,4R)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort
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