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Macrocyclic Carbohydrate/Amino Acid Hybrid Molecules - Synthesis and Evaluation as Artificial Receptors

Billing, Johan LU (2005)
Abstract
Methods were developed for the synthesis of three different types of macrocyclic carbohydrate/amino acid hybrid molecules. In the synthesis of the first type of macrocycles, a glucosamine derivative was oxidized at C6 and the obtained sugar amino acid was coupled to tripeptides. The resulting hybrids were transformed into dimers and cyclized in a macrolactamization step to obtain C2-symmetric macrocycles.



In the second type of macrocycles, the same sugar amino acid was used together with tyrosine to prepare a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues. In the synthesis of the third type of macrocycles, Cu(I)-catalysed 1,3-dipolar cycloaddition of azides and acetylenes was employed to... (More)
Methods were developed for the synthesis of three different types of macrocyclic carbohydrate/amino acid hybrid molecules. In the synthesis of the first type of macrocycles, a glucosamine derivative was oxidized at C6 and the obtained sugar amino acid was coupled to tripeptides. The resulting hybrids were transformed into dimers and cyclized in a macrolactamization step to obtain C2-symmetric macrocycles.



In the second type of macrocycles, the same sugar amino acid was used together with tyrosine to prepare a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues. In the synthesis of the third type of macrocycles, Cu(I)-catalysed 1,3-dipolar cycloaddition of azides and acetylenes was employed to form C2-symmetric carbohydrate/amino acid hybrid molecules containing two 1,2,3-triazole units.



The macrocycles that were water-soluble were screened for affinity towards biomolecules. Weak, but significant, affinity was found for dAMP, dGMP, serotonin and caffeine for some of the macrocycles (Ka approx. 10 M-1) which indicates that molecules of this type have potential as artificial receptors. Possibilities to extend the developed methods to prepare further types of macrocycles are discussed. (Less)
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author
supervisor
opponent
  • Assist. Professor Schweizer, Frank, University of Manitoba, Canada.
organization
publishing date
type
Thesis
publication status
published
subject
keywords
3-dipolar cycloaddition, 3-triazoles, 2, 1, molecular recognition, artificial receptors, sugar amino acids, cyclic peptides, macrocycles, Organic chemistry, Organisk kemi
publisher
Organic Chemistry, Lund University
defense location
Center for Chemistry and Chemical Engineering, Room K:C, Lund Institute of Technology.
defense date
2005-03-11 13:30
ISBN
91-628-6413-0
language
English
LU publication?
yes
id
06b98033-3518-423e-8bd6-e01c4c24298a (old id 544383)
date added to LUP
2007-10-13 11:48:32
date last changed
2016-09-19 08:45:09
@phdthesis{06b98033-3518-423e-8bd6-e01c4c24298a,
  abstract     = {Methods were developed for the synthesis of three different types of macrocyclic carbohydrate/amino acid hybrid molecules. In the synthesis of the first type of macrocycles, a glucosamine derivative was oxidized at C6 and the obtained sugar amino acid was coupled to tripeptides. The resulting hybrids were transformed into dimers and cyclized in a macrolactamization step to obtain C2-symmetric macrocycles.<br/><br>
<br/><br>
In the second type of macrocycles, the same sugar amino acid was used together with tyrosine to prepare a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues. In the synthesis of the third type of macrocycles, Cu(I)-catalysed 1,3-dipolar cycloaddition of azides and acetylenes was employed to form C2-symmetric carbohydrate/amino acid hybrid molecules containing two 1,2,3-triazole units.<br/><br>
<br/><br>
The macrocycles that were water-soluble were screened for affinity towards biomolecules. Weak, but significant, affinity was found for dAMP, dGMP, serotonin and caffeine for some of the macrocycles (Ka approx. 10 M-1) which indicates that molecules of this type have potential as artificial receptors. Possibilities to extend the developed methods to prepare further types of macrocycles are discussed.},
  author       = {Billing, Johan},
  isbn         = {91-628-6413-0},
  keyword      = {3-dipolar cycloaddition,3-triazoles,2,1,molecular recognition,artificial receptors,sugar amino acids,cyclic peptides,macrocycles,Organic chemistry,Organisk kemi},
  language     = {eng},
  publisher    = {Organic Chemistry, Lund University},
  school       = {Lund University},
  title        = {Macrocyclic Carbohydrate/Amino Acid Hybrid Molecules - Synthesis and Evaluation as Artificial Receptors},
  year         = {2005},
}