Ring structures and mutarotations of the modifications of D-galacturonic acid

Isbell, Horace S.; Frush, Harriet L.

doi:10.6028/jres.031.021

Cited by 11 publications

(5 citation statements)

References 7 publications

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“…n-Galakturonsaure-Monohydrat kristallisiert als a-Pyranosid (RE = 6,O bzw. 6,4)1) [9]. Durch Umkristallisation aus absolutem Alkohol oder durch Trocknung bei 60" iiber P,O, im Hochvakuum [lo] konnte diese Verbindung in das /?-Pyranosid (RE-Wert = 7,7 bzw.…”

Section: Gas-chromatographische Untersuchungen Anunclassified

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Gas‐chromatographische Untersuchungen an Uronsäuren und Uronsäurederivaten

Raunhardt

Schmidt

Neukom

1967

Helvetica Chimica Acta

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Das gas‐chromatographische Verhalten der Per‐trimethylsilyl‐Derivate einiger natürlich vorkommender Uronsäuren bzw. Uronolactone, ihrer Salze, ihrer Reduktions‐(Onsäuresalze und‐γ‐lactone) und Oxydationsprodukte (Glycarsäuren bzw. ihre Salze und Lactone) sowie ihrer Reaktionsprodukte mit Methanol wurde auf den Silikongummi‐Kolonnen SE‐52 und SE‐30 untersucht. Die beim Kochen von D‐Mannuron, D‐Glucuron und L‐Guluronsäure mit 2proz. methanolischer Salzsäure entstehenden Glycosidgemische wurden nach der Silylierung gas‐chromatographisch analysiert und die prozentuale Verteilung der auftretenden Pike nach Erreichen des Gleichgewichtes bestimmt. Anhand der gefundenen, auf meso‐Erythrit als internen Standard bezogenen Retentionszeiten wird die Trennbarkeit der Uronsäuren diskutiert.

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Section: Gas-chromatographische Untersuchungen Anunclassified

“…SE-30-Kolonne (zweite Zahl). ten 4,l (4,5) und 5,5 (5,9) gehoren offenbar zu den ,8bzw. a-Furanosidformen, denn die gleiche Reihenfolge wurde bei den Derivaten der vier isomeren Methyl-galakturonoside und der Methylestermethylglycoside (vgl.…”

Section: Gas-chromatographische Untersuchungen Anunclassified

Gas‐chromatographische Untersuchungen an Uronsäuren und Uronsäurederivaten

Raunhardt

Schmidt

Neukom

1967

Helvetica Chimica Acta

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“…D-Galactaro-δ-lactone was prepared in D 2 O via bromine oxidation of D-galacturonate. 8 This material could not be distinguished by 1 H nuclear magnetic resonance (NMR) spectroscopy from the product obtained by the NAD +dependent Udh (Atu3143). The synthetic δ-lactone is stable indefinitely at pD 4.8 and −80 °C.…”

mentioning

confidence: 99%

Galactaro δ-Lactone Isomerase: Lactone Isomerization by a Member of the Amidohydrolase Superfamily

Bouvier¹,

Groninger-Poe²,

Vetting

et al. 2014

Biochemistry

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Agrobacterium tumefaciens strain C58 can utilize d-galacturonate as a sole source of carbon via a pathway in which the first step is oxidation of d-galacturonate to d-galactaro-1,5-lactone. We have identified a novel enzyme, d-galactarolactone isomerase (GLI), that catalyzes the isomerizaton of d-galactaro-1,5-lactone to d-galactaro-1,4-lactone. GLI, a member of the functionally diverse amidohydrolase superfamily, is a homologue of LigI that catalyzes the hydrolysis of 2-pyrone-4,6-dicarboxylate in lignin degradation. The ability of GLI to catalyze lactone isomerization instead of hydrolysis can be explained by the absence of the general basic catalysis used by 2-pyrone-4,6-dicarboxylate lactonase.

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“…The observed value for the mutarotation constant of mannuronic lactone at 20° C (0.125) is much higher than the constant (0.0148) for the interconversion of the pyranose modifications of galacturonic acid [7], but it does not differ widely from that (0.16) found for the rapid mutarotation reaction of galacturonic acid hydrate, which was ascribed to a pyranose-furanose interconversion.…”

Section: Initial Rapid :Mutarotationmentioning

confidence: 72%

“…It has been shown also [7] that the two pyranose modifications of galacturonic acid on bromine oxidation yield an optically active lactone of mucic acid, a fact which demonstrates that the pyranose ring remains intact during the oxidation. 2 Thus the bromine oxidation method is applicable to the study of the ring structure of the uronic acids.…”

Section: Methodsmentioning

confidence: 99%

Mutarotation and ring structure of mannuronic lactone

Isbell¹,

Frush²

1946

J. RES. NATL. BUR. STAN.

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The numerous commercial applications of algin, a polysaccharide derived from certain marine plants, makes important the study of its principal constituent, D-mannuronic lactone. In 'this paper it is shown that by oxidation with bromine mannosaccharic dilactone of known structure is formed directly from mannuronic lactone without change in ring structure, and hence the latter SUbstance, like mannosaccharic dilactone, has a bicyclic structure consisting of two butylene oxide rings. The initial rapid mutarotation reaction of the substance is show n to consist of a conversion of the beta furanose modification to an equilibrium mixture containing the alpha furanose, and a detectable amount of the aldehyde modification. There is a small but measurable displacement of equilibrium with change in temperature. The mutarotation is exceptionslly sensitive to basic catalysts and for this reason the point of minimum rate lies in the acid region at pH 3.1.

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Ring structures and mutarotations of the modifications of D-galacturonic acid

Cited by 11 publications

References 7 publications

Gas‐chromatographische Untersuchungen an Uronsäuren und Uronsäurederivaten

Gas‐chromatographische Untersuchungen an Uronsäuren und Uronsäurederivaten

Galactaro δ-Lactone Isomerase: Lactone Isomerization by a Member of the Amidohydrolase Superfamily

Mutarotation and ring structure of mannuronic lactone

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