NMR Characterization of 3,6-Dioxa-8-azabicyclo[3.2.1]octanes and N-[Tris(hydroxymethyl)methyl]alanine Formed from Methylglyoxal in Tris Buffer Solutions
✍ Scribed by William A. Bubb
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 450 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
The reactions of methylglyoxal in aqueous solutions of Tris [ tris(hydroxymethyl)aminomethane ] bu †er were examined at 600 MHz by two-dimensional NMR experiments selected to circumvent the difficulties associated with spectral assignment in the presence of intense resonances due to both solvent and bu †er. Methylglyoxal, generated in situ from glyceraldehyde 3-phosphate, reacted with Tris to yield principally a mixture of 3,6-dioxa-8azabicyclo [ 3.2.1 ] octanes. 1H and 13C NMR parameters are reported for three compounds containing this littleknown ring system and structural inÑuences compared with those in related compounds. A much slower reaction led to the ultimate formation of N-[ tris(hydroxymethyl)methyl ] alanine. Implications for various enzyme assays are considered and the results are compared with previous observations of reactions of a-dicarbonyl compounds with a-amino alcohols.
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