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

Johan Billing

Research output: ThesisDoctoral Thesis (compilation)

577 Downloads (Pure)

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 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.
Original languageEnglish
QualificationDoctor
Awarding Institution
  • Centre for Analysis and Synthesis
Supervisors/Advisors
  • Nilsson, Ulf, Supervisor
Award date2005 Mar 11
Publisher
Print ISBNs91-628-6413-0
Publication statusPublished - 2005

Bibliographical note

Defence details

Date: 2005-03-11
Time: 13:30
Place: Center for Chemistry and Chemical Engineering, Room K:C, Lund Institute of Technology.

External reviewer(s)

Name: Schweizer, Frank
Title: Assist. Professor
Affiliation: University of Manitoba, Canada.

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<div class="article_info">Johan F. Billing and Ulf J. Nilsson. <span class="article_issue_date">2005</span>. <a href="javascript:downloadFile(544392)" class="article_link">Cyclic peptides containing a delta-sugar amino acid-synthesis and evaluation as artificial receptors</a> <span class="journal_series_title">Tetrahedron</span>, <span class="journal_volume">vol 61</span> <span class="journal_pages">pp 863-874</span>. <span class="journal_distributor">Elsevier Science</span></div>
<div class="article_info">Johan F. Billing and Ulf J. Nilsson. <span class="article_issue_date">2005</span>. <a href="javascript:downloadFile(544393)" class="article_link">Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues</a> <span class="journal_series_title">Tetrahedron letters</span>, <span class="journal_volume">vol 46</span> <span class="journal_pages">pp 991-993</span>. <span class="journal_distributor">Elsevier</span></div>
<div class="article_info">Johan F. Billing and Ulf J. Nilsson. <span class="article_issue_date"></span>. <span class="article_title">C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles</span> (manuscript)</div>
<div class="article_info">Johan F. Billing and Ulf J. Nilsson. <span class="article_issue_date"></span>. <span class="article_title">Synthesis of an O-benzyl protected delta-sugar amino acid tert-butyl ester</span> (manuscript)</div>
<div class="article_info">Johan F. Billing and Ulf J. Nilsson. <span class="article_issue_date">2005</span>. <a href="javascript:downloadFile(544394)" class="article_link">Supplementary material : Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues</a> <span class="journal_series_title">Tetrahedron Letters</span>, <span class="journal_volume">vol 46</span> <span class="journal_distributor">Elsevier</span></div>
<div class="article_info">. <span class="article_issue_date">2005</span>. <span class="article_title">jfjf</span> (submitted)</div>


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)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

  • 3-dipolar cycloaddition
  • 3-triazoles
  • 2
  • 1
  • molecular recognition
  • artificial receptors
  • sugar amino acids
  • cyclic peptides
  • macrocycles
  • Organic chemistry
  • Organisk kemi

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