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

doi:10.1016/j.tet.2013.04.033

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

Charnwood Technical Consulting Ltd

Research output: Contribution to journal › Article › peer-review

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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 language	English
Pages (from-to)	5989-5997
Journal	Tetrahedron
Volume	69
Issue number	29
Early online date	18 Apr 2013
DOIs	https://doi.org/10.1016/j.tet.2013.04.033
Publication status	Published - 22 Jul 2013

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Bioengineering

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10.1016/j.tet.2013.04.033

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This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Corresponding author Email: [email protected].
Final published version, 1.28 MBLicence: CC BY

Cite this

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

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.",

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AU - Griffen, Julia

AU - White, J

AU - Kociok-Kohn, Gabriele

AU - Lloyd, Matthew

AU - Wells, Andrew

AU - Arnot, Tom

AU - Lewis, Simon

PY - 2013/7/22

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N2 - 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.

AB - 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.

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

Abstract

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MC2- Nuclear Magnetic Resonance (NMR)

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Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

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