New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho-arene dihydrodiol

Julia Griffen, J White, Gabriele Kociok-Kohn, Matthew Lloyd, Andrew Wells, Tom Arnot, Simon Lewis

Research output: Contribution to journalArticle

28 Citations (Scopus)
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Abstract

Microbial ipso,ortho-dihydroxylation of benzoic acid by the B9 mutant strain of Ralstonia eutropha permits rapid construction of aminocyclitols containing a quaternary stereocentre. Installation of the amine functionality is achieved by use of an acylnitroso dienophile for a hetero-Diels–Alder reaction. Both aminotetrols and aminohexols are accessible as single enantiomers by this route. Both NOESY spectroscopic and x-ray crystallographic analyses were required to distinguish cycloadduct isomers. Notably, subsequent to the biooxidation step, all new stereocentres are installed under substrate control. Thus, all stereochemical information is ultimately of enzymatic origin.
Original languageEnglish
Pages (from-to)5989-5997
JournalTetrahedron
Volume69
Issue number29
Early online date18 Apr 2013
DOIs
Publication statusPublished - 22 Jul 2013

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Cupriavidus necator
Benzoic Acid
Cycloaddition
Enantiomers
Benzoic acid
Cycloaddition Reaction
Isomers
Amines
X-Rays
X rays
Substrates
trans-1,2-dihydro-1,2-naphthalenediol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Bioengineering

Cite this

New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho-arene dihydrodiol. / Griffen, Julia; White, J; Kociok-Kohn, Gabriele; Lloyd, Matthew; Wells, Andrew; Arnot, Tom; Lewis, Simon.

In: Tetrahedron, Vol. 69, No. 29, 22.07.2013, p. 5989-5997.

Research output: Contribution to journalArticle

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