Abstract
The further optimization of 3-ketodisaccharide formation with sucrose, leucrose and iso maltutose was studied with special regard to pH and oxygen concentration in the reaction mixture with resting cells of Agrobacterium tumefaciens. It was found that the optimal pH values for the highest reaction rate and highest yield were different as the pH affected the stability of the 3-keto derivatives formed. A pH shift to 5.0 clearly reduced the enzymatic degradation of the 3-keto derivatives thus stabilizing them. The influence of constant oxygen concentrations on 3-ketosucrose formation was tested showing results not explicable with normal Michaelis-Menten kinetics. For each substrate a maximum of reaction rate and yield were obtained at very low oxygen concentrations.
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References
Bernaerts MJ, De Ley J (1958) 3-Ketoglycosides, new intermediates in the bacterial catabolism of disaccharides. Biochim Biophys Acta 30:661–662
Bernaerts MJ, De Ley J (1960) Microbial Formation and Preparation of 3-ketoglycosides from disaccharides. J Gen Microbiol 22:129–136
Buchholz K, Stoppok E, Matalla K, Reh KD, Jördening HJ (1991) Enzymatic sucrose modification and saccharide synthesis. In: Lichtenthaler FW (ed) Carbohydrates as organic raw materials. Verlag Chemie, Weinheim New York Basel, pp 155–168
Buchholz K, Stoppok E, Noll-Borchers M, Walter J, Pietsch M, Walter M (1993) Selektive biochemische Oxidation und chemische Funktionalisierung von Disacchariden. In: Schriftenreihe des Bundesministers für Ernährung, Landwirtschaft und Forsten, Reihe A. 2. Symposium Nachwachsende Rohstoffe —Perspektiven für die Chemie, 5–6 Mai 1993, Frankfurt. Landwirtschaftsverlag, pp 217–233
Fukui S, Hayano K (1969) Micro method for determination of 3-ketosucrose and 3-ketoglucose. Agric Biol Chem 33:1013–1017
Fukui S, Hochster RM (1963) Conversion of disaccharides to the corresponding glycoside-3-uloses by intact cells Agrobacterium tumefaciens. Can J Biochem Biophys 41:2363–2371
Hisamatsu M, Sano K, Amemura A, Harada T (1978) Acidic polysaccharides containing succinic acid in various strains of Agrobacterium. Carbohydr Res 61:89–96
Janssens D, Kersters K, De Ley J (1983) The catabolism of 3-ketolactose in Agrobacterium. System Appl Microbiol 4:155–168
Klekner V, Löbl V, Šimová E, Novák M (1989) Conversion of disaccharides to 3-ketodisaccharides by nongrowing and immobilized cells of Agrobacterium tumefaciens. Folia Microbiol 34: 286–293
Kurowski WM, Darbyshire J (1978) The production of 3-ketosucrose by Agrobacterium tumefaciens in batch culture. J Appl Chem Biotechnol 28:638–640
Matalla K (1991) Untersuchungen zur Oxidation von Disacchariden mit Agrobacterium tumefaciens. PhD Thesis, Technical University Braunschweig
Noll-Borchers M (1992) Selektive mikrobielle und chemische Derivatisierung von Isomaltulose für die Herstellung von Polymeren auf Saccharidbasis. PhD Thesis, Technical University Braunschweig
Noll-Borchers M, Buchholz K (1993) Kinetics and yields of 3-ketoisomaltulose by microbial oxidation of isomaltulose. Biotechnol Lett 15:139–144
Pietsch M (1993) Untersuchungen zu Stabilität und Reaktivität sowie speziellen Derivaten der 3-Keto-Saccharose. PhD Thesis, Technical Univesity Braunschweig
Pietsch M, Walter M, Buchholz K (1994) Regioselective synthesis of new sucrose derivatives via 3-ketosucrose. Carbohydr Res 254:183–194
Schwengers D, Benecke H (1984) Süβungsmittel, Verfahren zur Herstellung und Verwendung desselben. DBP-DE 34 46 380
Schwengers D, Benecke H (1985) Süβungsmittel, Verfahren zur Herstellung und Verwendung desselben. European patent 185 302
Stoppok E, Matalla K, Buchholz K (1992) Microbial modification of sugars as building blocks for chemicals. Appl Microbiol Biotechnol 36:604–610
Tyler DD, Nakamura LK (1971) Conditions for production of 3-ketomaltose from Agrobacterium tumefaciens. Appl Microbiol 21:175–180
Walter J (1994) Kinetik der Bildung von 3-Keto-Disacchariden mit Agrobacterium tumefaciens und chemische Folgereaktionen mit 3-Keto-Leucrose. PhD Thesis, Technical University Braunschweig
Walter J, Stoppok E, Buchholz K (1991) Einfluβgröβen der biotechnologischen Oxidation des Disaccharids Leucrose. Chem-Ing-Tech 63:631–633
Zevenhuizen LPTM (1973) Methylation analysis of acidic exopolysaccharides of Rhizobium and Agrobacterium. Carbohydr Res 26:409–419
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Dedicated to Professor Dr. Fritz Wagner on the occasion of his 65th birthday
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Stoppok, E., Walter, J. & Buchholz, K. The effect of pH and oxygen concentration on the formation of 3-ketodisaccharides by Agrobacterium tumefaciens . Appl Microbiol Biotechnol 43, 706–712 (1995). https://doi.org/10.1007/BF00164777
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DOI: https://doi.org/10.1007/BF00164777