Synthesis towards an aromatic alfa-dixyloside
(2015) KOK820 20111Centre for Analysis and Synthesis
- Abstract
- A proteoglycan is a protein with at least one glycosidic chain or glycosaminoglycan (GAG) covalently bound to it. Since a common linker between the core protein and the GAG chain has a xylose present, the biosynthesis of GAGs can be primed using xylosides containing hydrophobic aglycons providing that these xylosides are capable of penetrating the cell membrane.
2-naphthyl β-D-xylopyranoside primes synthesis of chondroitin sulfate/dermatan sulfate and heparan sulfate/heparin as showed by Mani et. al. and in addition 2-(6-hydroxynaphthyl) β-D-xylopyranoside also shows selective antiproliferative effect between normal cells and cancer cells. Also Bakker et. al recently showed that oligosaccharides containing dixylopyranosides linked α1-3... (More) - A proteoglycan is a protein with at least one glycosidic chain or glycosaminoglycan (GAG) covalently bound to it. Since a common linker between the core protein and the GAG chain has a xylose present, the biosynthesis of GAGs can be primed using xylosides containing hydrophobic aglycons providing that these xylosides are capable of penetrating the cell membrane.
2-naphthyl β-D-xylopyranoside primes synthesis of chondroitin sulfate/dermatan sulfate and heparan sulfate/heparin as showed by Mani et. al. and in addition 2-(6-hydroxynaphthyl) β-D-xylopyranoside also shows selective antiproliferative effect between normal cells and cancer cells. Also Bakker et. al recently showed that oligosaccharides containing dixylopyranosides linked α1-3 show biological activity in mammalian cells. These findings gave the idea that α–linked aromatic dixylopyranosides might prime GAG synthesis, if their polarity allows them to penetrate the cell membrane, and show antiproliferative effect.
In this report, a synthetic pathway towards an aromatic dixyloside 2-naphthyl α-D-xylopyranoside-(1-4)-1-O-α-D-xylopyranoside was attempted using α-selective O-glycosylation with thioxylosides on aromatic xylosides with suitable protective groups. An aromatic α-dixyloside was indeed produced in somewhat low yields, but the last deprotection step in the synthetic pathway tended to break the glycosidic bond between the xylosides. (Less) - Popular Abstract
- Cancer is a group of about 200 different diseases where cells division and growth occurs at an uncontrollable rate in the body. Most cancer diseases are treatable with chemotherapy, but the effectiveness of the chemotherapy is often strictly limited by the toxicity towards other tissues and other side effects on the patient.
A xylose containing a hydrophobic aromatic aglycon can interrupt a biosynthetic process in cancer cells and tricks it into producing a compound which is toxic to the cell. In this project, we investigated a synthetic pathway towards an aromatic dixyloside, but the last deprotection step in the synthetic pathway tended to break the glycosidic bond between the xylosides instead of removing the intended protective... (More) - Cancer is a group of about 200 different diseases where cells division and growth occurs at an uncontrollable rate in the body. Most cancer diseases are treatable with chemotherapy, but the effectiveness of the chemotherapy is often strictly limited by the toxicity towards other tissues and other side effects on the patient.
A xylose containing a hydrophobic aromatic aglycon can interrupt a biosynthetic process in cancer cells and tricks it into producing a compound which is toxic to the cell. In this project, we investigated a synthetic pathway towards an aromatic dixyloside, but the last deprotection step in the synthetic pathway tended to break the glycosidic bond between the xylosides instead of removing the intended protective group. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/7360064
- author
- Olofsson, Martin LU
- supervisor
- organization
- alternative title
- Syntes mot en aromatisk alfa-dixyloside
- course
- KOK820 20111
- year
- 2015
- type
- H2 - Master's Degree (Two Years)
- subject
- keywords
- Synthesis, Proteoglycan, Glucosaminoglycan, Xylose, Carbohydrate, Glycosylation, Organic chemistry
- language
- English
- id
- 7360064
- date added to LUP
- 2024-02-28 12:49:57
- date last changed
- 2024-02-28 12:49:57
@misc{7360064,
abstract = {{A proteoglycan is a protein with at least one glycosidic chain or glycosaminoglycan (GAG) covalently bound to it. Since a common linker between the core protein and the GAG chain has a xylose present, the biosynthesis of GAGs can be primed using xylosides containing hydrophobic aglycons providing that these xylosides are capable of penetrating the cell membrane.
2-naphthyl β-D-xylopyranoside primes synthesis of chondroitin sulfate/dermatan sulfate and heparan sulfate/heparin as showed by Mani et. al. and in addition 2-(6-hydroxynaphthyl) β-D-xylopyranoside also shows selective antiproliferative effect between normal cells and cancer cells. Also Bakker et. al recently showed that oligosaccharides containing dixylopyranosides linked α1-3 show biological activity in mammalian cells. These findings gave the idea that α–linked aromatic dixylopyranosides might prime GAG synthesis, if their polarity allows them to penetrate the cell membrane, and show antiproliferative effect.
In this report, a synthetic pathway towards an aromatic dixyloside 2-naphthyl α-D-xylopyranoside-(1-4)-1-O-α-D-xylopyranoside was attempted using α-selective O-glycosylation with thioxylosides on aromatic xylosides with suitable protective groups. An aromatic α-dixyloside was indeed produced in somewhat low yields, but the last deprotection step in the synthetic pathway tended to break the glycosidic bond between the xylosides.}},
author = {{Olofsson, Martin}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis towards an aromatic alfa-dixyloside}},
year = {{2015}},
}