Reaktionen der glucuronsäure

Dax, K.; Weidmann, H

doi:10.1016/s0008-6215(00)81646-8

Cited by 13 publications

(1 citation statement)

References 24 publications

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“…Preparation of 1,2-0-Isopropylidene-a-D-[5,6,6'-2H2]glucofuranose. The 5-keto derivative of 1,2-O-isopropylidene-a-D-glucofuranurono-6,3-lactone was prepared from the 1,2-0-isopropylidene-a-D-glucofuranurono-6,3-lactone 5nitrate by base elimination of nitrite ion as described by Dax and Weidmann (1972). The resulting keto compound was reduced with sodium borohydride as described by Mackie and Berlin (1965).…”

Section: Methodsmentioning

confidence: 99%

Stable isotope studies on the biosynthesis of the thiazole moiety of thiamin in Escherichia coli

White¹

1978

Biochemistry

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Deuterated and 13C-labeled sugars were fed to Escherichia coli growing on defined medium. The position and extent of incorporation of the label into the 4-methyl-5-beta-hydroxyethylthiazole portion of thiamin and other cellular components were measured by gas chromatography-mass spectrometry. Based on the findings, it is concluded that the contiguous five-carbon unit of the 4-methyl-5-beta-hydroxyethylthiazole is biosynthetically derived from pyruvate and a triose phosphate.

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Section: Methodsmentioning

confidence: 99%

Stable isotope studies on the biosynthesis of the thiazole moiety of thiamin in Escherichia coli

White¹

1978

Biochemistry

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Monosaccharide mit stickstoffhaltigem Ring, XXXV. Untersuchungen zur Darstellung von 5‐Amino‐5‐desoxyhexuronsäuren

Paulsen

Günther

1977

Chem. Ber.

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N , N -D i e t h y l -l , 2 -O -~s o p r o p y l i d e n -3 , 5 -d i -~-m e s y l -a -~-g l u r e a m i d(2 b) reagiert mit Azid-Ionen unter S,Z-Substitution und Inversion am C-5 zur L-ido-Verbindung 3. Eine Nachbargruppenreaktion der N,N-Diethylcarboxamidgruppe, wie sie beim Einsatz von Acetat-Ionen beobachtet wird, tritt nicht ein. Die Konfiguration von 3 wurde durch Rontgenstrukturanalyse bestimmt. Die Elementarzelle der Kristalle von 3 enthalt zwei symmetrie-unabhangige Molekiile, die unterschiedliche Konformationen aufweisen. Der Furanosering zeigt in einem Molekiil eine E,-im anderen eine 'T,-Konformation. Die Aminonitrilsynthese des D-ribo-Aldehyds 8 liefert ein 1 : 1-Gemisch der ~-0110-und L-talo-Aminonitrile 10a und 11 a. Monosaccharides Containing Nitrogen in the Ring, XXXV ') Investigations into the Synthesis of 5-Amino-5-deoxyhexuronic AcidsThe reaction of N,N-diethyl-l,2-O-isopropylidene-3.5-di-O-mesyl-a-~-glucofuranuronamide (2 b) with azide ions proceeds uia an SN2 substitution with inversion at C-5 and yields the L-ido derivative 3. A neighbouring-group participation of the N,N-diethylcarboxamide group does not occur, as observed by the application of acetate ions. The configuration of 3 was determined by X-ray structure analysis. The crystals of 3 have two symmetrically independent molecules per unit, each of them having different conformations. The furanoid rings correspond with the E, conformation and with the 3T4 conformation, respectively. The aminonitrile synthesis of the D-ribo aldehyde 8 yields a 1 : 1 mixture of D-allo-and L-talo-aminonitriles 10a and 11 a. Ware eine entsprechende Umsetzung unter Retention auch mit anderen Nucleophilen, wie Azid, moglich, so stande ein Syntheseweg offen zur Gewinnung der 5-Azido-und ') XXXIV. Mitteil.: H.

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Total Synthesis of the Gastroprotective Substance AI‐77‐B and of Analogues

Durgant¹,

Vogel²

1993

Helvetica Chimica Acta

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The Diels-Alder adducts 8 of furan to I-cyanovinyl acetate were converted into (methyl 3-chloro-5-0-(3-chlorohenzoyl)-2,3-dideoxy-cc -DL-arahino -hexofuranosid)uronic acid ((&)-Ma) and into (methyl 3-azido-5-0 -(3-chlorobenzoyl)-2,3-dideoxy-a -DL-riho -hexofuranosid)uronic acid ((+)-4la). These compounds were condensed to (3S)-3-[(1'S)-1'-amino-3'-methylbutyl]-3,4-dihydro-8-hydroxyisoconinarin hydrochloride ((-)-2); the resulting mixtures of diastereoisomeric amides were transformed and separated to give the gastroprotective substance AI-77-B ((-)-1) and analogues.

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Reaktionen der glucuronsäure

Cited by 13 publications

References 24 publications

Stable isotope studies on the biosynthesis of the thiazole moiety of thiamin in Escherichia coli

Stable isotope studies on the biosynthesis of the thiazole moiety of thiamin in Escherichia coli

Monosaccharide mit stickstoffhaltigem Ring, XXXV. Untersuchungen zur Darstellung von 5‐Amino‐5‐desoxyhexuronsäuren

Total Synthesis of the Gastroprotective Substance AI‐77‐B and of Analogues

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