Synthesis of aromatic C-xylosides by position inversion of glucose

Jesper Malmberg; Katrin Mani; Elin Säwén; Anders Wiren; Ulf Ellervik

doi:10.1016/j.bmc.2006.05.068

Synthesis of aromatic C-xylosides by position inversion of glucose

Jesper Malmberg, Katrin Mani, Elin Säwén, Anders Wiren, Ulf Ellervik

Research output: Contribution to journal › Article › peer-review

Abstract

Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6659-6665
Journal	Bioorganic & Medicinal Chemistry
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.bmc.2006.05.068
Publication status	Published - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)

Subject classification (UKÄ)

Medicinal Chemistry

Free keywords

structure-activity relationships
C-glycosides
carbohydrates
xylose

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10.1016/j.bmc.2006.05.068

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title = "Synthesis of aromatic C-xylosides by position inversion of glucose",

abstract = "Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "structure-activity relationships, C-glycosides, carbohydrates, xylose",

author = "Jesper Malmberg and Katrin Mani and Elin S{\"a}w{\'e}n and Anders Wiren and Ulf Ellervik",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)",

year = "2006",

doi = "10.1016/j.bmc.2006.05.068",

language = "English",

volume = "14",

pages = "6659--6665",

journal = "Bioorganic & Medicinal Chemistry",

issn = "0968-0896",

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TY - JOUR

T1 - Synthesis of aromatic C-xylosides by position inversion of glucose

AU - Malmberg, Jesper

AU - Mani, Katrin

AU - Säwén, Elin

AU - Wiren, Anders

AU - Ellervik, Ulf

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)

PY - 2006

Y1 - 2006

N2 - Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

KW - structure-activity relationships

KW - C-glycosides

KW - carbohydrates

KW - xylose

U2 - 10.1016/j.bmc.2006.05.068

DO - 10.1016/j.bmc.2006.05.068

M3 - Article

SN - 0968-0896

VL - 14

SP - 6659

EP - 6665

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 19

ER -

Synthesis of aromatic C-xylosides by position inversion of glucose

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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