Structures of Novel Acidic Galactooligosaccharides Synthesized by<i>Bacillus circulans</i>β-Galactosidase

Yanahira, Shuichi; Yabe, Yukiko; Nakakoshi, Masamichi; Miura, Susumu; Matsubara, Noriaki; Ishikawa, Hidetoshi

doi:10.1271/bbb.62.1791

Cited by 19 publications

(12 citation statements)

References 16 publications

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“…12) GN was a mixture of Gal(β1 8)Neu5Ac (45%), Gal(β1 9)Neu5Ac (45%) and Gal(β1 3)Gal(β1 8) Neu5Ac (10%). Sialyllactose (SL) was separated from cheese whey as follows.…”

Section: Methodsmentioning

confidence: 99%

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Effects of Feeding Sialyllactose and Galactosylated N-Acetylneuraminic Acid on Swimming Learning Ability and Brain Lipid Composition in Adult Rats

Sakai¹,

Ikeuchi²,

Urashima³

et al. 2006

J. Appl. Glycosci.

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Sialic acid, which occurs at the non reducing ends of carbohydrate moieties of animal glycoproteins and gangliosides, and of free oligosaccharides in milk colostrum, 1 3) has many biological functions. 4) It is generally considered that sialic acid inhibits the attachment of pathogenic viruses, bacteria and bacterial toxins to the epithelial cells in the colon, bronchus and lung, etc. 5,6) and that sialic acid in brain gangliosides participates in synaptogenesis and neural transmission. 3,7) As sialic acid is also contained in carbohydrate moieties of the glycoconjugates in foods, including milk or colostrums, 8 11) both infants and adults consume sialic acid in their diets. Wang and Brand Miller have suggested that sialic acid from glycoconjugates of milk may be absorbed in the infant small intestine and be used for brain ganglioside formation. 3,7)The absorption of sialic acid in the small intestine has not, however, been fully established to date.In this study, we fed sialyllactose, which has been found in bovine colostrum and cheese whey, or galactosylated N acetylneuraminic acid, which had been synthesized as described in our previous study, 12) to adult rats, and studied their swimming learning behavior and brain lipid composition. MATERIAL AND METHODS Materials.Free N acetylneuraminic acid (Neu5Ac) was commercially obtained from Snow Brand Milk Products Co., Ltd. Galactosylated N acetylneuraminic acid (GN) was synthesized from Neu5Ac and lactose with Bacillus circulans β galactosidase as described in our previous paper.12) GN was a mixture of Gal(β1 8)Neu5Ac (45%), Gal(β1 9)Neu5Ac (45%) and Gal(β1 3)Gal(β1 8) Neu5Ac (10%). Sialyllactose (SL) was separated from cheese whey as follows. 13,14) Cheese whey (1500 kg) was concentrated by evaporation and the lactose partially removed by crystallization. The supernatant was passed through an anion exchange resin (Dowex 1 × 4), which was then eluted with a large volume of water to wash out non acidic solutes. The SL, which had been adsorbed by the resin, was eluted using a linear gradient of 0 0.06 M sodium acetate. The eluate was deionized using electron dialysis and lyophilized to obtain 96% pure SL of which 87% was Neu5Ac(α2 3)Gal(β1 4)Glc and 13% was Neu5 Ac(α2 6)Gal(β1 4)Glc, as determined by high performance liquid chromatography. Galactooligosaccharide (GL) was prepared by a transglycosylation reaction catalyzed by Aspergillus oryzae β galactosidase according to the method of Deya et al .15) The GL was purified by charcoal column chromatography. The composition of GL was 75% trisaccharide, 20% tetrasaccharide and 5% pentasaccharide. The main structure was Gal(β1 6)Gal(β1 4)Glc.Animals and Diets. Thirty six male Sprague Dawley (SD) rats (8 weeks: Charles River Inc.), with an initial mean weight of 300 g, were housed under controlled ambient temperature (22±2 C) conditions with 55±5% humidity and lighting (light cycle from to 12 h) with free access to food and water. The control group (n=6) was fed the AIN 96G (Oriental Yeast Co., Ltd.) diet while the treated...

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“…12) GN was a mixture of Gal(β1 8)Neu5Ac (45%), Gal(β1 9)Neu5Ac (45%) and Gal(β1 3)Gal(β1 8) Neu5Ac (10%). Sialyllactose (SL) was separated from cheese whey as follows.…”

Section: Methodsmentioning

confidence: 99%

“…In this study, we fed sialyllactose, which has been found in bovine colostrum and cheese whey, or galactosylated N acetylneuraminic acid, which had been synthesized as described in our previous study, 12) to adult rats, and studied their swimming learning behavior and brain lipid composition.…”

mentioning

confidence: 99%

Effects of Feeding Sialyllactose and Galactosylated N-Acetylneuraminic Acid on Swimming Learning Ability and Brain Lipid Composition in Adult Rats

Sakai¹,

Ikeuchi²,

Urashima³

et al. 2006

J. Appl. Glycosci.

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“…The signals were assigned by using 1 H-1 H COSY, 1 H-13 C HMQC, and 1 H-13 C HMBC, and comparing with the chemical shifts in the reference data. [24][25][26] Furthermore, the configurations of anomeric carbons were defined from their coupling constants. In assigning the galactooligosaccharide moiety, the linkage site of the rhamnosyl residue with the galactosyl residue was first fixed by considering factors such as shifting of the chemical shifts in the 1 H-NMR and 13 C-NMR spectra.…”

Section: Identification Of the Enzymatically Synthesized Compoundsmentioning

confidence: 99%

Enzymatic Production of Highly Soluble Myricitrin Glycosides Using β-Galactosidase

Shimizu

Shimabayashi

Moriwaki

2006

Bioscience, Biotechnology, and Biochemistry

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“…4,5,12,13) In particular, -galactosidase-2 does not require high lactose concentrations to produce high yields of oligosaccharides, in contrast to most -galactosidases reported to date. 4) -Galactosidase-2 produces GOS at a yield of about 41% from a 4.56% solution of lactose at 40 C. Hence, during the past 20 years, the commercial enzyme Biolacta Ò has frequently been utilized to synthesize various functional galactosylated compounds [32][33][34][35][36][37][38][39][40][41][42] as well as GOS. 5,9,12,13,43,44) In a later study, Vetere et al 45) isolated a third enzyme, with a molecular mass of 86 kDa, from Biolacta Ò , but they did not study oligosaccharide production.…”

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confidence: 99%

Causes of the Production of Multiple Forms of β-Galactosidase byBacillus circulans

Song

Abe

Imanaka

et al. 2011

Bioscience, Biotechnology, and Biochemistry

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Structures of Novel Acidic Galactooligosaccharides Synthesized byBacillus circulansβ-Galactosidase

Cited by 19 publications

References 16 publications

Effects of Feeding Sialyllactose and Galactosylated N-Acetylneuraminic Acid on Swimming Learning Ability and Brain Lipid Composition in Adult Rats

Effects of Feeding Sialyllactose and Galactosylated N-Acetylneuraminic Acid on Swimming Learning Ability and Brain Lipid Composition in Adult Rats

Enzymatic Production of Highly Soluble Myricitrin Glycosides Using β-Galactosidase

Causes of the Production of Multiple Forms of β-Galactosidase byBacillus circulans

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