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Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues

Billing, Johan LU and Nilsson, Ulf LU orcid (2005) In Tetrahedron Letters 46(6). p.991-993
Abstract
A C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was subsequently elongated to the trimer via the dimer, and finally cyclized to give the C3-symmetric macrocycle.
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author
and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
46
issue
6
pages
991 - 993
publisher
Elsevier
external identifiers
  • wos:000226714000023
  • scopus:12344268871
ISSN
0040-4039
DOI
10.1016/j.tetlet.2004.12.038
language
English
LU publication?
yes
additional info
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
25f42b12-5d86-4cf4-a1cb-13d7be17354e (old id 158666)
date added to LUP
2016-04-01 16:02:35
date last changed
2025-12-04 03:11:56
@article{25f42b12-5d86-4cf4-a1cb-13d7be17354e,
  abstract     = {{A C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was subsequently elongated to the trimer via the dimer, and finally cyclized to give the C3-symmetric macrocycle.}},
  author       = {{Billing, Johan and Nilsson, Ulf}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  number       = {{6}},
  pages        = {{991--993}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues}},
  url          = {{http://dx.doi.org/10.1016/j.tetlet.2004.12.038}},
  doi          = {{10.1016/j.tetlet.2004.12.038}},
  volume       = {{46}},
  year         = {{2005}},
}