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

Johan Billing

Forskningsoutput: AvhandlingDoktorsavhandling (sammanläggning)

581 Nedladdningar (Pure)

Sammanfattning

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.
Originalspråkengelska
KvalifikationDoktor
Tilldelande institution
  • Centrum för analys och syntes
Handledare
  • Nilsson, Ulf, handledare
Tilldelningsdatum2005 mar 11
Förlag
Tryckta ISBN91-628-6413-0
StatusPublished - 2005

Bibliografisk information

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)

Ämnesklassifikation (UKÄ)

  • Organisk kemi

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