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Synthetic studies on naphthoxylosides - labeled compounds and mechanistic studies on acetals

Johnsson, Richard LU (2008)
Abstract
Labeled analogs to an antiproliferative naphthoxyloside have been synthesized and evaluated. Our investigations have shown that the fluorescently labeled analogs are poor structural analogs, and the physical and biological properties are altered to a large extent. Instead, a radioactively labeled compound was synthesized, which made it possible to follow the pathway in the cell. The results showed a difference between a normal and a transformed cell line based on accumulation of the naphthoxyloside and it appears that the transformed cells process the naphthoxylosides faster than the normal cells do.



This work also involved mechanistic studies for regioselective openings of benzylidene acetals with boranes and a new... (More)
Labeled analogs to an antiproliferative naphthoxyloside have been synthesized and evaluated. Our investigations have shown that the fluorescently labeled analogs are poor structural analogs, and the physical and biological properties are altered to a large extent. Instead, a radioactively labeled compound was synthesized, which made it possible to follow the pathway in the cell. The results showed a difference between a normal and a transformed cell line based on accumulation of the naphthoxyloside and it appears that the transformed cells process the naphthoxylosides faster than the normal cells do.



This work also involved mechanistic studies for regioselective openings of benzylidene acetals with boranes and a new mechanism has been proposed. As it turns out, the regioselectivity can be controlled by the choice of borane, Lewis acid and solvent. When the borane is activated by a Lewis acid, the reaction rate is increased and the borane is the most electrophilic species, thus directing the regioselectivity. In contrary, when the borane is not activated, the Lewis acid is the most electrophilic species that directs the regioselectivity. (Less)
Please use this url to cite or link to this publication:
author
supervisor
opponent
  • Universitetslektor Almqvist, Fredrik, Organic Chemistry, Umeå University
organization
publishing date
type
Thesis
publication status
published
subject
keywords
Fluorescent xylosides, Carbohydrates, Naphthoxylosides, Cancer, Mechanistic studies, Radioactive xylosides, Acetals
pages
102 pages
publisher
Organic Chemistry, Lund University
defense location
Hörsal B; Kemicentrum, Getingevägen 60, Lunds Tekniska Högskola
defense date
2008-04-25 09:30
ISBN
978-91-628-7473-5
language
English
LU publication?
yes
id
500f5811-818e-4491-8ff7-8ce9f1d32f36 (old id 1051679)
date added to LUP
2008-03-31 11:46:06
date last changed
2016-09-19 08:45:08
@misc{500f5811-818e-4491-8ff7-8ce9f1d32f36,
  abstract     = {Labeled analogs to an antiproliferative naphthoxyloside have been synthesized and evaluated. Our investigations have shown that the fluorescently labeled analogs are poor structural analogs, and the physical and biological properties are altered to a large extent. Instead, a radioactively labeled compound was synthesized, which made it possible to follow the pathway in the cell. The results showed a difference between a normal and a transformed cell line based on accumulation of the naphthoxyloside and it appears that the transformed cells process the naphthoxylosides faster than the normal cells do.<br/><br>
<br/><br>
This work also involved mechanistic studies for regioselective openings of benzylidene acetals with boranes and a new mechanism has been proposed. As it turns out, the regioselectivity can be controlled by the choice of borane, Lewis acid and solvent. When the borane is activated by a Lewis acid, the reaction rate is increased and the borane is the most electrophilic species, thus directing the regioselectivity. In contrary, when the borane is not activated, the Lewis acid is the most electrophilic species that directs the regioselectivity.},
  author       = {Johnsson, Richard},
  isbn         = {978-91-628-7473-5},
  keyword      = {Fluorescent xylosides,Carbohydrates,Naphthoxylosides,Cancer,Mechanistic studies,Radioactive xylosides,Acetals},
  language     = {eng},
  pages        = {102},
  publisher    = {ARRAY(0x84108f8)},
  title        = {Synthetic studies on naphthoxylosides - labeled compounds and mechanistic studies on acetals},
  year         = {2008},
}