Claisen-type addition of glycine to a pyridoxal iminium ion in water

Krisztina Toth; Lauren M. Gaskell; John P. Richard

doi:10.1021/jo061090e

Claisen-type addition of glycine to a pyridoxal iminium ion in water

Krisztina Toth
, Lauren M. Gaskell
, John P. Richard

Chemistry

SUNY Buffalo

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

9 Scopus citations

Abstract

The 5′-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH ≥ 8, this carbanion reacts with the iminium carbon of the pyridoxalglycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

Original language	English
Pages (from-to)	7094-7096
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	71
Issue number	18
DOIs	https://doi.org/10.1021/jo061090e
State	Published - Sep 1 2006

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title = "Claisen-type addition of glycine to a pyridoxal iminium ion in water",

abstract = "The 5′-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH ≥ 8, this carbanion reacts with the iminium carbon of the pyridoxalglycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.",

author = "Krisztina Toth and Gaskell, \{Lauren M.\} and Richard, \{John P.\}",

year = "2006",

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AU - Toth, Krisztina

AU - Gaskell, Lauren M.

AU - Richard, John P.

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Y1 - 2006/9/1

N2 - The 5′-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH ≥ 8, this carbanion reacts with the iminium carbon of the pyridoxalglycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

AB - The 5′-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH ≥ 8, this carbanion reacts with the iminium carbon of the pyridoxalglycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

UR - https://www.scopus.com/pages/publications/33750484987

U2 - 10.1021/jo061090e

DO - 10.1021/jo061090e

M3 - Article

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SP - 7094

EP - 7096

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Claisen-type addition of glycine to a pyridoxal iminium ion in water

Abstract

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