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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
Author(s) -
Bubb William A.
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199703)35:3<191::aid-omr54>3.0.co;2-c
Subject(s) - tris , methylglyoxal , chemistry , hydroxymethyl , solvent , carbon 13 nmr , aqueous solution , proton nmr , yield (engineering) , organic chemistry , stereochemistry , enzyme , biochemistry , materials science , metallurgy
The reactions of methylglyoxal in aqueous solutions of Tris [tris(hydroxymethyl)aminomethane] buffer 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 buffer. Methylglyoxal, generated in situ from glyceraldehyde 3‐phosphate, reacted with Tris to yield principally a mixture of 3,6‐dioxa‐8‐azabicyclo[3.2.1]octanes. 1 H and 13 C NMR parameters are reported for three compounds containing this little‐known ring system and structural influences 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 α‐dicarbonyl compounds with α‐amino alcohols. © 1997 by John Wiley & Sons, Ltd.