Branched deoxyaldaric acids from alkaline degradation of carbohydrates: Structure determination by mass spectrometry of trimethylsilyl derivatives

• The deoxyaldaric acids corresponding in structure to the 3-deoxy-2-C-(hydroxymethyl)aldonic (isosaccharinic) acids have been identified as products of treatment of various carbohydrates with alkali and oxygen-alkali. The structures of the acids were determined from the mass spectra of their Me3Si derivatives on the basis of previously known, specific fragmentation reactions. The g.l.c.-m.s. technique was used, and g.l.c. retention data are given. The identified species are 2-deoxy-3-C-(hydroxymethyl)tetraric, 3-deoxy-2-C-hydroxymethyl-erythro-pentaric, 3-deoxy-2-C-hydroxymethyl-threo-pentaric, 2-methyltartronic, 2-(2-hydroxyethyl)tartronic, and 2-(2,3-dihydroxypropyl)tartronic acids. Their formation from 4-O-substituted uronic and ulosonic acids is briefly discussed.

Subject headings

NATURVETENSKAP  -- Kemi -- Analytisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Analytical Chemistry (hsv//eng)

TEKNIK OCH TEKNOLOGIER  -- Kemiteknik (hsv//swe)

ENGINEERING AND TECHNOLOGY  -- Chemical Engineering (hsv//eng)

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

hydroxy dicarboxylic acids

trimethylsilyl derivatives

GC - MS

alkaline degradation

carbohydrates

Publication and Content Type

art (subject category)

ref (subject category)