Some non-anomerically C-C-linked carbohydrate amino acids related to leucine - synthesis and structure determination

• (5'R)-5'-Isobutyl-5'-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5'-R configuration was confirmed by X-ray crystallography. Corresponding α-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-α-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-β-L-erythrofuranosid-4-C-yl]-D-leucine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5S configuration, formed in a minority, were also isolated and characterised.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)

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

Keyword

Leucine

Bucherer–Bergs reaction

3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose

Methyl 6-deoxy-6-isopropyl-2

Hydantoins

X-ray crystallography

Sugar amino acids

Publication and Content Type

art (subject category)

ref (subject category)