Studies on the reactivity of azetidin-2-ones in phosphate buffer

Nicholas James Westwood; CJ Schofield; TDW Claridge

doi:10.1039/a702673k

Studies on the reactivity of azetidin-2-ones in phosphate buffer

Nicholas James Westwood
, CJ Schofield
, TDW Claridge

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

Abstract

H-1 NMP (500 MHz) analyses repeal that in phosphate buffer, N-arylsulfonyl beta-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hydrolysis and via an unstable acyl phosphate intermediate, The acyl phosphate intermediates can be trapped using hydrazine.

Original language	English
Pages (from-to)	2725-2729
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	18
DOIs	https://doi.org/10.1039/a702673k
Publication status	Published - 21 Sept 1997

Keywords

HUMAN-LEUKOCYTE ELASTASE

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title = "Studies on the reactivity of azetidin-2-ones in phosphate buffer",

abstract = "H-1 NMP (500 MHz) analyses repeal that in phosphate buffer, N-arylsulfonyl beta-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hydrolysis and via an unstable acyl phosphate intermediate, The acyl phosphate intermediates can be trapped using hydrazine.",

keywords = "HUMAN-LEUKOCYTE ELASTASE",

author = "Westwood, \{Nicholas James\} and CJ Schofield and TDW Claridge",

year = "1997",

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language = "English",

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journal = "Journal of the Chemical Society, Perkin Transactions 1",

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TY - JOUR

T1 - Studies on the reactivity of azetidin-2-ones in phosphate buffer

AU - Westwood, Nicholas James

AU - Schofield, CJ

AU - Claridge, TDW

PY - 1997/9/21

Y1 - 1997/9/21

N2 - H-1 NMP (500 MHz) analyses repeal that in phosphate buffer, N-arylsulfonyl beta-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hydrolysis and via an unstable acyl phosphate intermediate, The acyl phosphate intermediates can be trapped using hydrazine.

AB - H-1 NMP (500 MHz) analyses repeal that in phosphate buffer, N-arylsulfonyl beta-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hydrolysis and via an unstable acyl phosphate intermediate, The acyl phosphate intermediates can be trapped using hydrazine.

KW - HUMAN-LEUKOCYTE ELASTASE

UR - https://www.scopus.com/pages/publications/33748594493

U2 - 10.1039/a702673k

DO - 10.1039/a702673k

M3 - Article

SN - 0300-922X

SP - 2725

EP - 2729

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 18

ER -

Studies on the reactivity of azetidin-2-ones in phosphate buffer

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