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Esterification of borate with NAD+ and NADH as studied by electrospray ionization mass spectrometry and 11B NMR spectroscopy

✍ Scribed by Danny H. Kim; Beth N. Marbois; Kym F. Faull; Curtis D. Eckhert

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
426 KB
Volume
38
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

This paper describes for the first time the direct measurement of boric acid (B(OH)~3~) and borate (B(OH)~4~^−^) adduction to NAD^+^ and NADH by electrospray ionization mass spectrometry (ESI‐MS) and ^11^B NMR spectroscopy. The analysis demonstrates that borate binds to both cis‐2,3‐ribose diols on NAD^+^ forming borate monoesters (1 : 1 addition), borate diesters (1 : 2 addition) and diborate esters (2 : 1 addition), whereas, only borate monoesters were formed with NADH. MS in the negative ion mode showed borate was bound to a cis‐2,3‐ribose diol and not to the hydroxyl groups on the phosphate backbone of NAD^+^, and MS/MS showed that the 1 : 1 addition monoester contained borate bound to the adenosine ribose. Boron shifts of borate monoesters and diesters with NAD^+^ were observed at 7.80 and 12.56 ppm at pH 7.0 to 9.0. The esterifications of borate with NAD^+^ and NADH were pH dependent with maximum formation occurring under alkaline conditions with significant formation occurring at pH 7.0. Using ESI‐MS, the limit of detection was 50 µM for NAD^+^ and boric acid (1 : 1) to detect NAD^+^–borate monoester at pH 7.0. These results suggest esterification of borate with nicotinamide nucleotides could be of biological significance. Copyright © 2003 John Wiley & Sons, Ltd.

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