Abstract Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.
AbstractList Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.
Author Morawitz, Falk
Fuszard, Matthew A.
Smellie, Iain A.
Botting, Catherine H.
Smith, Margaret C. M.
Bent, Andrew F.
Shirran, Sally L.
Houssen, Wael E.
Jaspars, Marcel
Naismith, James H.
Koehnke, Jesko
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  surname: Shirran
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  fullname: Smellie, Iain A.
  organization: Biomedical Science Research Complex, University of St Andrews, North Haugh, St. Andrews, KY16 9ST (UK)
– sequence: 8
  givenname: Catherine H.
  surname: Botting
  fullname: Botting, Catherine H.
  organization: Biomedical Science Research Complex, University of St Andrews, North Haugh, St. Andrews, KY16 9ST (UK)
– sequence: 9
  givenname: Margaret C. M.
  surname: Smith
  fullname: Smith, Margaret C. M.
  organization: Institute of Medical Sciences, University of Aberdeen, Ashgrove Road West, Aberdeen, AB25 2ZD (UK)
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  givenname: Marcel
  surname: Jaspars
  fullname: Jaspars, Marcel
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  givenname: James H.
  surname: Naismith
  fullname: Naismith, James H.
  email: naismith@st-and.ac.uk
  organization: Biomedical Science Research Complex, University of St Andrews, North Haugh, St. Andrews, KY16 9ST (UK)
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Snippet Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic...
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SubjectTerms Amino Acid Sequence
biochemistry
biosynthesis
Communications
Cysteine - chemistry
Cysteine - metabolism
Iodoacetamide - chemistry
Multienzyme Complexes - metabolism
Oxazoles - chemistry
Oxazoles - metabolism
patellamides
Peptides, Cyclic - biosynthesis
Peptides, Cyclic - chemistry
selenazolines
Selenium - chemistry
Selenium - metabolism
Selenocysteine - chemistry
Selenocysteine - metabolism
Serine - chemistry
Serine - metabolism
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Thiazoles - chemistry
Thiazoles - metabolism
Threonine - chemistry
Threonine - metabolism
Title An Enzymatic Route to Selenazolines
URI https://api.istex.fr/ark:/67375/WNG-NCFX0KT8-V/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcbic.201300037
https://www.ncbi.nlm.nih.gov/pubmed/23483642
https://www.proquest.com/docview/1315994197
https://pubmed.ncbi.nlm.nih.gov/PMC3625746
Volume 14
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