Hydrolysis of nitrite esters: Putative intermediates in the biotransformation of organic nitrates

Felicity Buckell; Jeffrey D. Hartry; Umarani Rajalingam; Brian M. Bennett; Ralph A. Whitney; Gregory R.J. Thatcher

doi:10.1039/p29940000401

Hydrolysis of nitrite esters: Putative intermediates in the biotransformation of organic nitrates

Felicity Buckell
, Jeffrey D. Hartry
, Umarani Rajalingam
, Brian M. Bennett
, Ralph A. Whitney
, Gregory R.J. Thatcher

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

17 Scopus citations

Abstract

Study and comparison of the pH-independent hydrolysis of eight alkyl nitrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediate in the biotransformation of glyceryl trinitrate, to be unexpectedly reactive and too labile to be detected as a biotransformation intermediate in aqueous solution, suggesting a role for neighbouring group participation by the β-nitrate group.

Original language	English (US)
Pages (from-to)	401-403
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	3
DOIs	https://doi.org/10.1039/p29940000401
State	Published - 1994
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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10.1039/p29940000401

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title = "Hydrolysis of nitrite esters: Putative intermediates in the biotransformation of organic nitrates",

abstract = "Study and comparison of the pH-independent hydrolysis of eight alkyl nitrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediate in the biotransformation of glyceryl trinitrate, to be unexpectedly reactive and too labile to be detected as a biotransformation intermediate in aqueous solution, suggesting a role for neighbouring group participation by the β-nitrate group.",

author = "Felicity Buckell and Hartry, \{Jeffrey D.\} and Umarani Rajalingam and Bennett, \{Brian M.\} and Whitney, \{Ralph A.\} and Thatcher, \{Gregory R.J.\}",

year = "1994",

doi = "10.1039/p29940000401",

language = "English (US)",

pages = "401--403",

journal = "Journal of the Chemical Society, Perkin Transactions 2",

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T1 - Hydrolysis of nitrite esters

T2 - Putative intermediates in the biotransformation of organic nitrates

AU - Buckell, Felicity

AU - Hartry, Jeffrey D.

AU - Rajalingam, Umarani

AU - Bennett, Brian M.

AU - Whitney, Ralph A.

AU - Thatcher, Gregory R.J.

PY - 1994

Y1 - 1994

N2 - Study and comparison of the pH-independent hydrolysis of eight alkyl nitrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediate in the biotransformation of glyceryl trinitrate, to be unexpectedly reactive and too labile to be detected as a biotransformation intermediate in aqueous solution, suggesting a role for neighbouring group participation by the β-nitrate group.

AB - Study and comparison of the pH-independent hydrolysis of eight alkyl nitrites shows 3-nitroso-1,2-glyceryl dinitrate, a putative intermediate in the biotransformation of glyceryl trinitrate, to be unexpectedly reactive and too labile to be detected as a biotransformation intermediate in aqueous solution, suggesting a role for neighbouring group participation by the β-nitrate group.

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UR - https://www.scopus.com/pages/publications/37049076918#tab=citedBy

U2 - 10.1039/p29940000401

DO - 10.1039/p29940000401

M3 - Article

AN - SCOPUS:37049076918

SN - 1472-779X

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EP - 403

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

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ER -

Hydrolysis of nitrite esters: Putative intermediates in the biotransformation of organic nitrates

Abstract

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