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Synthesis and structure determination of some glycoconjugates related to mannojirimycin and serine

Julia Micova ; Bohumil Steiner ; Miroslav Koós ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Dalma Gyepesová
ChemZi (1336-7242). Vol. 1 (2005), 1, p. 222-223.
[Konferensbidrag, övrigt]

Glycoconjugates of lipids and proteins represent a very important group of organic compounds. Due to their responsibility for recognition in biological events, there is growing interest in the use of synthetic glycopeptides as model compounds.

(5S)-5-Triphenylmethoxymethyl-[5-methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2,4-dione(1) was synthesized from methyl 6-O-trityl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose and applying the Bucherer-Bergs reaction. As a minor product, the isomer 3 with 5-R configuration was isolated. Corresponding α-amino acids 5 and 6 were obtained from the above hydantoins by the selective acid hydrolysis of the trityl and isopropylidene groups followed by basic hydrolysis of the hydantoin ring. 2-Oxazolidinone derivate 7 instead of the expected hydantoin was obtained starting from 6-O-unprotected 5-ulose.

The configuration at C-5' atom was unambiguosly established by single-crystal X-ray diffraction analysis of the hydantoin derivative 2.

Nyckelord: syntesis, X-ray analysis

Denna post skapades 2006-08-25.
CPL Pubid: 8312


Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)



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