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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 (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
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
id
25f42b12-5d86-4cf4-a1cb-13d7be17354e (old id 158666)
date added to LUP
2007-07-10 09:16:29
date last changed
2017-09-24 04:22:55
@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},
  volume       = {46},
  year         = {2005},
}