ISSN:
1573-4986
Keywords:
Lacto-N-tetraose
;
lacto-N-neotetraose
;
β-D-galactosidase
;
β-1,3-N-acetylglucosaminyltransferase
;
LNT, lacto-N-tetraose (Galβ1-3GlcNAcβ1-3Galβ1-4Glc)
;
LNnT, lacto-N-neotetraose (Galβ1-4GlcNAcβ1-3Galβ1-4Glc)
;
UDP, uridine 5′-diphosphate
;
β-gal-3, β-D-galactosidase from Bacillus circulans ATCC 31382
;
β-1,3-GnT β-1,3-N-acetylglucosaminyltransferase
;
HPAEC-PAD
;
high performance anion exchange chromatography-pulsed amperometric detection
;
ATP, adenosine 5′-triphosphate
;
EtOH ethanol
;
Galβ-oNP
;
o-nitrophenyl β-D-galactopyranoside
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Lacto-N-tetraose (Galβ1-3GlcNAcβ1-3Galβ1-4Glc, LNT) and lacto-N-neotetraose (Galβ1-4GlcNAcβ1-3Galβ1-4Glc, LNnT) were enzymatically synthesized by consecutive additions of GlcNAc and Gal residues to lactose. Lacto-N-triose II (GlcNAcβ1-3Galβ1-4Glc) was prepared first by the transfer of GlcNAc from UDP-GlcNAc to lactose by β-1,3-N-acetylglucosaminyltransferase from bovine serum. The resulting lacto-N-triose II was converted into LNT and LNnT utilizing two kinds of β-D-galactosidase-mediated transglycosylations. Thus, β-D-galactosidase from Bacillus circulans ATCC31382 induced regioselective galactosyl transfer from o-nitrophenyl β-D-galactoside to the OH-3″ position of lacto-N-triose II, and commercially available β-D-galactosidase from B. circulans to the OH-4″ position of lacto-N-triose II. These convenient processes are suitable for large-scale preparations of LNT and LNnT. As another method, LNT was directly synthesized from lactose as an initial substance, utilizing lacto-N-biosidase (Aureobacterium sp. L-101)-mediated transglycosylation with Galβ1-3GlcNAcβ-pNP donor.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1007020219275
Permalink