Claisen-type addition of glycine to pyridoxal in water

Journal of the American Chemical Society

Volumn 126, Issue 34, 2004, Pages 10538-10539

  Toth, Krisztina ^a   Amyes, Tina L ^a   Richard, John P ^a   Malthouse, J Paul G ^b   NíBeilliú, Máire E ^b  

^a UNIVERSITY AT BUFFALO   (United States)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALANINE; CARBON DIOXIDE; DEUTERIUM; DEUTERIUM OXIDE; GLYCINE; PYRIDOXAL 5 PHOSPHATE; WATER;

ACIDITY; ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CLAISEN REARRANGEMENT; DIASTEREOISOMER; MOLECULAR STABILITY; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

ALANINE; GLYCINE; PYRIDOXAL PHOSPHATE; WATER;

EID: 4344606655     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047501v     Document Type: Article

References (25)

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4. - (1 mM).
5. 13C with a 0.54 s acquisition time, a 90° pulse angle, and a 7.8 s relaxation delay. The chemical shifts for the enriched carbons of the iminium ion adduct of glycine with 1 and the major and minor diastereomers of 2 are 55.6, 59.7, and 59.2 ppm, respectively.
6. 2O at pD 7.0.5
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8. 4) C, H, N. We have not determined the relative stereochemistry of the major and minor diastereomeric products so that either 2a or 2b could be the major product of the reaction of glycine with 1.
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13. 2O at pH 6.5.
14. o = 0.10 mM was followed directly by monitoring the decrease in absorbance at 412 nm (Figure 1).
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