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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 13:30:00
ISBN
91-628-6413-0
language
English
LU publication?
yes
additional info
Johan F. Billing and Ulf J. Nilsson. 2005. Cyclic peptides containing a delta-sugar amino acid-synthesis and evaluation as artificial receptors Tetrahedron, vol 61 pp 863-874. Elsevier Science
Johan F. Billing and Ulf J. Nilsson. 2005. Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues Tetrahedron letters, vol 46 pp 991-993. Elsevier
Johan F. Billing and Ulf J. Nilsson. . C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles (manuscript)
Johan F. Billing and Ulf J. Nilsson. . Synthesis of an O-benzyl protected delta-sugar amino acid tert-butyl ester (manuscript)
Johan F. Billing and Ulf J. Nilsson. 2005. Supplementary material : Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues Tetrahedron Letters, vol 46 Elsevier
. 2005. jfjf (submitted)
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)
id
06b98033-3518-423e-8bd6-e01c4c24298a (old id 544383)
date added to LUP
2016-04-04 11:23:18
date last changed
2018-11-21 21:04:31
@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}},
  keywords     = {{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}},
  url          = {{https://lup.lub.lu.se/search/files/5762016/544393.pdf}},
  year         = {{2005}},
}