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Volumn 27, Issue 1, 2010, Pages 125-132

Syntheses of mucin-type O-glycopeptides and oligosaccharides using transglycosylation and reverse-hydrolysis activities of Bifidobacterium endo-α-N-acetylgalactosaminidase

Author keywords

Bifidobacteria; Endoglycosidase; GH101; Mucin; O glycan; Prebiotics

Indexed keywords

ALPHA N ACETYLGALACTOSAMINIDASE; BRADYKININ; GALACTOSAMINE; GLUCOSE; GLYCAN DERIVATIVE; GLYCOPEPTIDE; LACTOSE; MUCIN; MUCIN 1; MUCIN 1A; N ACETYLGALACTOSAMINE; OLIGOSACCHARIDE; PEPTIDE; PEPTIDE T; PREBIOTIC AGENT; SERINE; STOMACH MUCIN; THREONINE; UNCLASSIFIED DRUG;

EID: 77949275251     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-009-9247-8     Document Type: Article
Times cited : (13)

References (27)
  • 1
    • 62649171202 scopus 로고    scopus 로고
    • Emerging methods for the production of homogeneous human glycoproteins
    • 10.1038/nchembio.148 10.1038/nchembio.148 1:CAS:528:DC%2BD1MXjtlWmtbg%3D 19295526
    • JR Rich SG Withers 2009 Emerging methods for the production of homogeneous human glycoproteins Nat. Chem. Biol. 5 206 215 10.1038/nchembio.148 10.1038/nchembio.148 1:CAS:528:DC%2BD1MXjtlWmtbg%3D 19295526
    • (2009) Nat. Chem. Biol. , vol.5 , pp. 206-215
    • Rich, J.R.1    Withers, S.G.2
  • 2
    • 0027290031 scopus 로고
    • Transglycosylation activity of endoglycoceramidase from Corynebacterium sp
    • 10.1006/abbi.1993.1461 10.1006/abbi.1993.1461 1:CAS:528: DyaK3sXmsVChsr0%3D 8373194
    • H Ashida Y Tsuji K Yamamoto H Kumagai T Tochikura 1993 Transglycosylation activity of endoglycoceramidase from Corynebacterium sp Arch. Biochem. Biophys. 305 559 562 10.1006/abbi.1993.1461 10.1006/abbi.1993.1461 1:CAS:528: DyaK3sXmsVChsr0%3D 8373194
    • (1993) Arch. Biochem. Biophys. , vol.305 , pp. 559-562
    • Ashida, H.1    Tsuji, Y.2    Yamamoto, K.3    Kumagai, H.4    Tochikura, T.5
  • 3
    • 0027989307 scopus 로고
    • Transglycosylation activity of Mucor hiemalis endo-β-N- acetylglucosaminidase which transfers complex oligosaccharides to the N-acetylglucosamine moieties of peptides
    • DOI 10.1006/bbrc.1994.2174
    • K Yamamoto S Kadowaki J Watanabe H Kumagai 1994 Transglycosylation activity of Mucor hiemalis endo-β-N-acetyl-glucosaminidase which transfers complex oligosaccharides to the N-acetylglucosamine moieties of peptides Biochem. Biophys. Res. Commun. 203 244 252 10.1006/bbrc.1994.2174 10.1006/bbrc.1994.2174 1:CAS:528:DyaK2MXmtFeksQ%3D%3D 8074662 (Pubitemid 24281086)
    • (1994) Biochemical and Biophysical Research Communications , vol.203 , Issue.1 , pp. 244-252
    • Yamamoto, K.1    Kadowaki, S.2    Watanabe, J.3    Kumagai, H.4
  • 4
    • 0034650455 scopus 로고    scopus 로고
    • Characterization of endo-α-N-acetylgalactosaminidase from Bacillus sp. and syntheses of neo-oligosaccharides using its transglycosylation activity
    • DOI 10.1006/abbi.1999.1565
    • H Ashida K Yamamoto T Murata T Usui H Kumagai 2000 Characterization of endo-α-N-acetylgalactosaminidase from Bacillus sp. and syntheses of neo-oligosaccharides using its transglycosylation activity Arch. Biochem. Biophys. 373 394 400 10.1006/abbi.1999.1565 10.1006/abbi.1999.1565 1:CAS:528:DC%2BD3cXosVGn 10620364 (Pubitemid 30068978)
    • (2000) Archives of Biochemistry and Biophysics , vol.373 , Issue.2 , pp. 394-400
    • Ashida, H.1    Yamamoto, K.2    Murata, T.3    Usui, T.4    Kumagai, H.5
  • 5
    • 0035961369 scopus 로고    scopus 로고
    • Enzymatic syntheses of T antigen-containing glycolipid mimicry using the transglycosylation activity of endo-α-N-acetylgalactosaminidase
    • DOI 10.1016/S0008-6215(01)00008-8, PII S0008621501000088
    • H Ashida K Yamamoto H Kumagai 2001 Enzymatic syntheses of T antigen-containing glycolipid mimicry using the transglycosylation activity of endo-α-N-acetylgalactosaminidase Carbohydr. Res. 330 487 493 10.1016/S0008-6215(01)00008-8 10.1016/S0008-6215(01)00008-8 1:CAS:528: DC%2BD3MXhslOntb0%3D 11269400 (Pubitemid 32206389)
    • (2001) Carbohydrate Research , vol.330 , Issue.4 , pp. 487-493
    • Ashida, H.1    Yamamoto, K.2    Kumagai, H.3
  • 6
    • 41949130819 scopus 로고    scopus 로고
    • Mutants of Mucor hiemalis endo-β-N-acetylglucosaminidase show enhanced transglycosylation and glycosynthase-like activities
    • 10.1074/jbc.M707137200 10.1074/jbc.M707137200 1:CAS:528: DC%2BD1cXhvFeltb0%3D 18096701
    • M Umekawa W Huang B Li K Fujita H Ashida LX Wang, et al. 2008 Mutants of Mucor hiemalis endo-β-N-acetylglucosaminidase show enhanced transglycosylation and glycosynthase-like activities J. Biol. Chem. 283 4469 4479 10.1074/jbc.M707137200 10.1074/jbc.M707137200 1:CAS:528: DC%2BD1cXhvFeltb0%3D 18096701
    • (2008) J. Biol. Chem. , vol.283 , pp. 4469-4479
    • Umekawa, M.1    Huang, W.2    Li, B.3    Fujita, K.4    Ashida, H.5    Wang, L.X.6
  • 7
    • 49449114141 scopus 로고    scopus 로고
    • Design of a sialylglycopolymer with a chitosan backbone having efficient inhibitory activity against influenza virus infection
    • 10.1021/jm8000967 10.1021/jm8000967 1:CAS:528:DC%2BD1cXovVGlsL0%3D 18651726
    • M Umemura M Itoh Y Makimura K Yamazaki M Umekawa A Masui, et al. 2008 Design of a sialylglycopolymer with a chitosan backbone having efficient inhibitory activity against influenza virus infection J. Med. Chem. 51 4496 4503 10.1021/jm8000967 10.1021/jm8000967 1:CAS:528:DC%2BD1cXovVGlsL0%3D 18651726
    • (2008) J. Med. Chem. , vol.51 , pp. 4496-4503
    • Umemura, M.1    Itoh, M.2    Makimura, Y.3    Yamazaki, K.4    Umekawa, M.5    Masui, A.6
  • 8
    • 27844482528 scopus 로고    scopus 로고
    • Identification and molecular cloning of a novel glycoside hydrolase family of core 1 type O-glycan-specific endo-α-N-acetylgalactosaminidase from Bifidobacterium longum
    • DOI 10.1074/jbc.M506874200
    • K Fujita F Oura N Nagamine T Katayama J Hiratake K Sakata, et al. 2005 Identification and molecular cloning of a novel glycoside hydrolase family of core 1 type O-glycan-specific endo-α-N-acetylgalactosaminidase from Bifidobacterium longum J. Biol. Chem. 280 37415 37422 10.1074/jbc.M506874200 10.1074/jbc.M506874200 1:CAS:528:DC%2BD2MXhtF2isrrJ 16141207 (Pubitemid 41642348)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.45 , pp. 37415-37422
    • Fujita, K.1    Oura, F.2    Nagamine, N.3    Katayama, T.4    Hiratake, J.5    Sakata, K.6    Kumagai, H.7    Yamamoto, K.8
  • 9
    • 0034672115 scopus 로고    scopus 로고
    • Diphenylamine-aniline-phosphoric acid reagent, a versatile spray reagent for revealing glycoconjugates on thin-layer chromatography plates
    • DOI 10.1006/abio.2000.4829
    • K Anderson SC Li YT Li 2000 Diphenylamine-aniline-phosphoric acid reagent, a versatile spray reagent for revealing glycoconjugates on thin-layer chromatography plates Anal. Biochem. 287 337 339 10.1006/abio.2000.4829 10.1006/abio.2000.4829 1:CAS:528:DC%2BD3cXosFGhtbs%3D 11112283 (Pubitemid 32006246)
    • (2000) Analytical Biochemistry , vol.287 , Issue.2 , pp. 337-339
    • Anderson, K.1    Li, S.-C.2    Li, Y.-T.3
  • 10
    • 0030769777 scopus 로고    scopus 로고
    • Purification and characterization of PAMP-12 (PAMP[9-20]) in porcine adrenal medulla as a major endogenous biologically active peptide
    • DOI 10.1016/S0014-5793(97)00971-X, PII S001457939700971X
    • K Kuwasako K Kitamura Y Ishiyama H Washimine J Kato K Kangawa, et al. 1997 Purification and characterization of PAMP-12 (PAMP[9-20]) in porcine adrenal medulla as a major endogenous biologically active peptide FEBS Lett. 414 105 110 10.1016/S0014-5793(97)00971-X 10.1016/S0014-5793(97)00971-X 1:CAS:528:DyaK2sXlslCit7Y%3D 9305741 (Pubitemid 27380364)
    • (1997) FEBS Letters , vol.414 , Issue.1 , pp. 105-110
    • Kuwasako, K.1    Kitamura, K.2    Ishiyama, Y.3    Washimine, H.4    Kato, J.5    Kangawa, K.6    Eto, T.7
  • 11
    • 0344702046 scopus 로고
    • The isolation of bradykinin, a plasma kinin from ox blood
    • 1:CAS:528:DyaF3MXjtlaqsw%3D%3D 13726430
    • DF Elliott EW Horton GP Lewis 1961 The isolation of bradykinin, a plasma kinin from ox blood Biochem. J. 78 60 65 1:CAS:528:DyaF3MXjtlaqsw%3D%3D 13726430
    • (1961) Biochem. J. , vol.78 , pp. 60-65
    • Elliott, D.F.1    Horton, E.W.2    Lewis, G.P.3
  • 12
    • 0025029968 scopus 로고
    • Molecular cloning and expression of human tumor-associated polymorphic epithelial mucin
    • 1:CAS:528:DyaK3MXlslKktA%3D%3D 1697589
    • SJ Gendler CA Lancaster J Taylor-Papadimitriou T Duhig N Peat J Burchell, et al. 1990 Molecular cloning and expression of human tumor-associated polymorphic epithelial mucin J. Biol. Chem. 265 15286 15293 1:CAS:528: DyaK3MXlslKktA%3D%3D 1697589
    • (1990) J. Biol. Chem. , vol.265 , pp. 15286-15293
    • Gendler, S.J.1    Lancaster, C.A.2    Taylor-Papadimitriou, J.3    Duhig, T.4    Peat, N.5    Burchell, J.6
  • 13
    • 0001508496 scopus 로고
    • Octapeptides deduced from the neuropeptide receptor-like pattern of antigen T4 in brain potently inhibit human immunodeficiency virus receptor binding and T-cell infectivity
    • 10.1073/pnas.83.23.9254 10.1073/pnas.83.23.9254 1:CAS:528: DyaL2sXkvVaqsw%3D%3D 3097649
    • CB Pert JM Hill MR Ruff RM Berman WG Robey LO Arthur, et al. 1986 Octapeptides deduced from the neuropeptide receptor-like pattern of antigen T4 in brain potently inhibit human immunodeficiency virus receptor binding and T-cell infectivity Proc. Natl Acad. Sci. USA 83 9254 9258 10.1073/pnas.83.23. 9254 10.1073/pnas.83.23.9254 1:CAS:528:DyaL2sXkvVaqsw%3D%3D 3097649
    • (1986) Proc. Natl Acad. Sci. USA , vol.83 , pp. 9254-9258
    • Pert, C.B.1    Hill, J.M.2    Ruff, M.R.3    Berman, R.M.4    Robey, W.G.5    Arthur, L.O.6
  • 14
    • 51449105672 scopus 로고    scopus 로고
    • Characterization of two different endo-α-N-acetylgalactosaminidases from probiotic and pathogenic enterobacteria
    • 10.1093/glycob/cwn053 1:CAS:528:DC%2BD1cXhtF2gsLzN
    • H Ashida R Maki H Ozawa Y Tani M Kiyohara M Fujita, et al. 2008 Characterization of two different endo-α-N-acetylgalactosaminidases from probiotic and pathogenic enterobacteria Bifidobacterium longum and Clostridium perfringens. Glycobiology 18 727 734 10.1093/glycob/cwn053 1:CAS:528: DC%2BD1cXhtF2gsLzN
    • (2008) Bifidobacterium Longum and Clostridium Perfringens. Glycobiology , vol.18 , pp. 727-734
    • Ashida, H.1    Maki, R.2    Ozawa, H.3    Tani, Y.4    Kiyohara, M.5    Fujita, M.6
  • 16
    • 0037234565 scopus 로고    scopus 로고
    • All in the family: The UDP-GalNAc:polypeptide N- acetylgalactosaminyltransferases
    • DOI 10.1093/glycob/cwg007
    • KG Ten Hagen TA Fritz LA Tabak 2003 All in the family: the UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferases Glycobiology 13 1R 16R 10.1093/glycob/cwg007 10.1093/glycob/cwg007 12634319 (Pubitemid 36372510)
    • (2003) Glycobiology , vol.13 , Issue.1
    • Ten Hagen, K.G.1    Fritz, T.A.2    Tabak, L.A.3
  • 17
    • 0035348528 scopus 로고    scopus 로고
    • Efficient Synthesis of O-Linked Glycopeptide by a Transglycosylation Using Endo α-N-Acetylgalactosaminidase from Streptomyces sp.
    • DOI 10.1271/bbb.65.1240
    • K Ajisaka M Miyasato I Ishii-Karakasa 2001 Efficient synthesis of O-linked glycopeptide by a transglycosylation using endo α-N- acetylgalactosaminidase from Streptomyces sp Biosci. Biotechnol. Biochem. 65 1240 1243 10.1271/bbb.65.1240 10.1271/bbb.65.1240 1:CAS:528:DC%2BD3MXktFaitrY%3D 11440149 (Pubitemid 33665990)
    • (2001) Bioscience, Biotechnology and Biochemistry , vol.65 , Issue.5 , pp. 1240-1243
    • Ajisaka, K.1    Miyasato, M.2    Ishii-Karakasa, I.3
  • 18
    • 40749160803 scopus 로고    scopus 로고
    • Mucin-type O-glycosylation and its potential use in drug and vaccine development
    • 1:CAS:528:DC%2BD1cXjsVSitrs%3D 17988798
    • MA Tarp H Clausen 2008 Mucin-type O-glycosylation and its potential use in drug and vaccine development Biochim. Biophys. Acta 1780 546 563 1:CAS:528:DC%2BD1cXjsVSitrs%3D 17988798
    • (2008) Biochim. Biophys. Acta , vol.1780 , pp. 546-563
    • Tarp, M.A.1    Clausen, H.2
  • 19
    • 26444477305 scopus 로고    scopus 로고
    • Di-tert-butylsilylene-directed α-selective synthesis of 4-methylumbelliferyl T-antigen
    • DOI 10.1021/ol051592z
    • A Imamura H Ando H Ishida M Kiso 2005 Di-tert-butylsilylene-directed α-selective synthesis of 4-methylumbelliferyl T-antigen Org. Lett. 7 4415 4418 10.1021/ol051592z 10.1021/ol051592z 1:CAS:528:DC%2BD2MXpsFartr0%3D 16178547 (Pubitemid 41436660)
    • (2005) Organic Letters , vol.7 , Issue.20 , pp. 4415-4418
    • Imamura, A.1    Ando, H.2    Ishida, H.3    Kiso, M.4
  • 20
    • 33845212293 scopus 로고    scopus 로고
    • Extended applications of di-tert-butylsilylene-directed α-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides
    • 1:CAS:528:DC%2BD28XhtlShtrbJ
    • A Imamura A Kimura H Ando H Ishida M Kiso 2006 Extended applications of di-tert-butylsilylene-directed α-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides Chemistry (Easton) 12 8862 8870 1:CAS:528:DC%2BD28XhtlShtrbJ
    • (2006) Chemistry (Easton) , vol.12 , pp. 8862-8870
    • Imamura, A.1    Kimura, A.2    Ando, H.3    Ishida, H.4    Kiso, M.5
  • 21
    • 59449106246 scopus 로고    scopus 로고
    • Di-tert-butylsilylene-directed α-selective synthesis of p-nitrophenyl T-antigen analogues
    • 10.1007/s10719-008-9168-y 10.1007/s10719-008-9168-y 1:CAS:528: DC%2BD1MXhtlOns70%3D 18709455
    • T Sato A Imamura H Ando H Ishida M Kiso 2009 Di-tert-butylsilylene- directed α-selective synthesis of p-nitrophenyl T-antigen analogues Glycoconj. J. 26 83 98 10.1007/s10719-008-9168-y 10.1007/s10719-008-9168-y 1:CAS:528:DC%2BD1MXhtlOns70%3D 18709455
    • (2009) Glycoconj. J. , vol.26 , pp. 83-98
    • Sato, T.1    Imamura, A.2    Ando, H.3    Ishida, H.4    Kiso, M.5
  • 23
    • 45149087204 scopus 로고    scopus 로고
    • Structural and thermodynamic analyses of solute-binding protein from Bifidobacterium longum specific for core 1 disaccharide and lacto-N-biose i
    • 10.1074/jbc.M709777200 10.1074/jbc.M709777200 1:CAS:528: DC%2BD1cXltlGqsr4%3D 18332142
    • R Suzuki J Wada T Katayama S Fushinobu T Wakagi H Shoun, et al. 2008 Structural and thermodynamic analyses of solute-binding protein from Bifidobacterium longum specific for core 1 disaccharide and lacto-N-biose I J. Biol. Chem. 283 13165 13173 10.1074/jbc.M709777200 10.1074/jbc.M709777200 1:CAS:528:DC%2BD1cXltlGqsr4%3D 18332142
    • (2008) J. Biol. Chem. , vol.283 , pp. 13165-13173
    • Suzuki, R.1    Wada, J.2    Katayama, T.3    Fushinobu, S.4    Wakagi, T.5    Shoun, H.6
  • 24
    • 20444393045 scopus 로고    scopus 로고
    • Novel putative galactose operon involving lacto-N-biose phosphorylase in Bifidobacterium longum
    • DOI 10.1128/AEM.71.6.3158-3162.2005
    • M Kitaoka J Tian M Nishimoto 2005 Novel putative galactose operon involving lacto-N-biose phosphorylase in Bifidobacterium longum Appl. Environ. Microbiol. 71 3158 3162 10.1128/AEM.71.6.3158-3162.2005 10.1128/AEM.71.6.3158- 3162.2005 1:CAS:528:DC%2BD2MXlt1Okur0%3D 15933016 (Pubitemid 40807225)
    • (2005) Applied and Environmental Microbiology , vol.71 , Issue.6 , pp. 3158-3162
    • Kitaoka, M.1    Tian, J.2    Nishimoto, M.3
  • 25
    • 34347335742 scopus 로고    scopus 로고
    • Identification of the putative proton donor residue of lacto-N-biose phosphorylase (EC 2.4.1.211)
    • DOI 10.1271/bbb.70064
    • M Nishimoto M Kitaoka 2007 Identification of the putative proton donor residue of lacto-N-biose phosphorylase (EC 2.4.1.211) Biosci. Biotechnol. Biochem 71 1587 1591 10.1271/bbb.70064 10.1271/bbb.70064 1:CAS:528: DC%2BD2sXnslyqu7o%3D 17587697 (Pubitemid 47012027)
    • (2007) Bioscience, Biotechnology and Biochemistry , vol.71 , Issue.6 , pp. 1587-1591
    • Nishimoto, M.1    Kitaoka, M.2
  • 26
    • 65449168413 scopus 로고    scopus 로고
    • The crystal structure of galacto-N-biose/lacto-N-biose i phosphorylase: A large deformation of a TIM barrel scaffold
    • 10.1074/jbc.M808525200 10.1074/jbc.M808525200 1:CAS:528: DC%2BD1MXislWqsb4%3D 19124470
    • M Hidaka M Nishimoto M Kitaoka T Wakagi H Shoun S Fushinobu 2009 The crystal structure of galacto-N-biose/lacto-N-biose I phosphorylase: a large deformation of a TIM barrel scaffold J. Biol. Chem. 284 7273 7283 10.1074/jbc.M808525200 10.1074/jbc.M808525200 1:CAS:528:DC%2BD1MXislWqsb4%3D 19124470
    • (2009) J. Biol. Chem. , vol.284 , pp. 7273-7283
    • Hidaka, M.1    Nishimoto, M.2    Kitaoka, M.3    Wakagi, T.4    Shoun, H.5    Fushinobu, S.6
  • 27
    • 70350455882 scopus 로고    scopus 로고
    • Crystallographic and mutational analyses on the substrate specificity of endo-α-N-acetylgalactosaminidase from Bifidobacterium longum
    • (Tokyo). in press. doi: 10.1093/jb/mvp086
    • Suzuki, R., Katayama, T., Ashida, H., Yamamoto, K., Kitaoka, M., Kumagai, H., et al.: Crystallographic and mutational analyses on the substrate specificity of endo-α-N-acetylgalactosaminidase from Bifidobacterium longum. J. Biochem. (Tokyo). in press. doi: 10.1093/jb/mvp086
    • J. Biochem.
    • Suzuki, R.1    Katayama, T.2    Ashida, H.3    Yamamoto, K.4    Kitaoka, M.5    Kumagai, H.6


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