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Volumn 3, Issue 1, 2008, Pages 114-121

2-Nitroglycals: Versatile intermediates for efficient and highly stereoselective base-catalyzed glycoside bond formations

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL; DISACCHARIDE; GALACTOSAMINE; GALACTOSE; GLYCAN; GLYCOSIDE; MUCIN; NITRIC ACID; SERINE; THREONINE;

EID: 38349091948     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2007.495     Document Type: Article
Times cited : (12)

References (41)
  • 1
    • 0027318961 scopus 로고
    • Biological roles of oligosaccharides: All of the theories are correct
    • Varki, A. Biological roles of oligosaccharides: All of the theories are correct. Glycobiology 3, 97-130 (1993).
    • (1993) Glycobiology , vol.3 , pp. 97-130
    • Varki, A.1
  • 2
    • 0032760680 scopus 로고    scopus 로고
    • Pathways of O-glycan biosynthesis in cancer cells
    • Brockhausen, I. Pathways of O-glycan biosynthesis in cancer cells. Biochem. Biophys. Acta 1473, 67-95 (1999).
    • (1999) Biochem. Biophys. Acta , vol.1473 , pp. 67-95
    • Brockhausen, I.1
  • 3
    • 0031023512 scopus 로고    scopus 로고
    • Glycosyl azides as building blocks in convergent syntheses of oligomeric lactosamine and Lewis(x) saccharides
    • Brocke, C. & Kunz, H. Glycosyl azides as building blocks in convergent syntheses of oligomeric lactosamine and Lewis(x) saccharides. Bioorg. Med. Chem. 5, 1-19 (1997).
    • (1997) Bioorg. Med. Chem , vol.5 , pp. 1-19
    • Brocke, C.1    Kunz, H.2
  • 4
    • 0026928690 scopus 로고
    • Mucins: Structure, function, and associations with malignancy
    • Devine, P.L. & McKenzie, I.F. Mucins: Structure, function, and associations with malignancy. Bioessays 14, 619-625 (1992).
    • (1992) Bioessays , vol.14 , pp. 619-625
    • Devine, P.L.1    McKenzie, I.F.2
  • 5
    • 0028867516 scopus 로고
    • Human mucin glycoproteins: Varied structures predict diverse properties and specific functions
    • Gum, J.R. Jr. Human mucin glycoproteins: Varied structures predict diverse properties and specific functions. Biochem. Soc. Trans. 23, 795-799 (1995).
    • (1995) Biochem. Soc. Trans , vol.23 , pp. 795-799
    • Gum Jr., J.R.1
  • 6
    • 0035137134 scopus 로고    scopus 로고
    • Roles of O-linked oligosaccharides in immune responses
    • Tsuboi, S. & Fukuda, M. Roles of O-linked oligosaccharides in immune responses. Bioessays 23, 46-53 (2001).
    • (2001) Bioessays , vol.23 , pp. 46-53
    • Tsuboi, S.1    Fukuda, M.2
  • 7
    • 0034599121 scopus 로고    scopus 로고
    • From the Laboratory to the clinic: A retrospective on fullysynthetic carbohydrate-based anticancer vaccines
    • Danishefsky, S.J. & Allen, J.R. From the Laboratory to the clinic: A retrospective on fullysynthetic carbohydrate-based anticancer vaccines. Angew. Chem. Int. Ed. Engl. 39, 836-863 (2000).
    • (2000) Angew. Chem. Int. Ed. Engl , vol.39 , pp. 836-863
    • Danishefsky, S.J.1    Allen, J.R.2
  • 8
    • 0035997381 scopus 로고    scopus 로고
    • Homogeneous glycopeptides and glycoproteins for biological investigation
    • Grogan, M.J., Pratt, M.R., Marcaurelle, L.A. & Bertozzi, C.R. Homogeneous glycopeptides and glycoproteins for biological investigation. Annu. Rev. Biochem. 71, 593-634 (2002).
    • (2002) Annu. Rev. Biochem , vol.71 , pp. 593-634
    • Grogan, M.J.1    Pratt, M.R.2    Marcaurelle, L.A.3    Bertozzi, C.R.4
  • 9
    • 84980170811 scopus 로고
    • Building units for oligosaccharides, IX. Stereoselective synthesis of α-glycosidically linked di- and oligosaccharides of 2-amino-2-deoxy-D-glucopyranose
    • Paulsen, H. & Stenzel, W. Building units for oligosaccharides, IX. Stereoselective synthesis of α-glycosidically linked di- and oligosaccharides of 2-amino-2-deoxy-D-glucopyranose. Chem. Ber. 111, 2334-2347 (1978).
    • (1978) Chem. Ber , vol.111 , pp. 2334-2347
    • Paulsen, H.1    Stenzel, W.2
  • 10
    • 84980140202 scopus 로고
    • Building units for oligosaccharides, X. Synthesis of α-(1>4) and α-(1 → 3) linked disaccharides of 2-amino-2-deoxy-D-glucopyranose by the azide method
    • Paulsen, H. & Stenzel, W. Building units for oligosaccharides, X. Synthesis of α-(1>4) and α-(1 → 3) linked disaccharides of 2-amino-2-deoxy-D-glucopyranose by the azide method. Chem. Ber. 111, 2348-2357 (1978).
    • (1978) Chem. Ber , vol.111 , pp. 2348-2357
    • Paulsen, H.1    Stenzel, W.2
  • 11
    • 0000776112 scopus 로고
    • Building units for oligosaccharides, XI. Synthesis of α glycosidically Linked di- and oligosaccharides of 2-amino-2-deoxy-D-galactopyranose
    • Paulsen, H., Kolar, C. & Stenzel, W. Building units for oligosaccharides, XI. Synthesis of α glycosidically Linked di- and oligosaccharides of 2-amino-2-deoxy-D-galactopyranose. Chem. Ber. 111, 2358-2369 (1978).
    • (1978) Chem. Ber , vol.111 , pp. 2358-2369
    • Paulsen, H.1    Kolar, C.2    Stenzel, W.3
  • 12
    • 84982495028 scopus 로고
    • Building units for oligosaccharides. XVI. Synthesis of the oligosaccharide determinants of the blood-group substances of type 1 of the ABH system
    • Paulsen, H. & Kolar, C. Building units for oligosaccharides. XVI. Synthesis of the oligosaccharide determinants of the blood-group substances of type 1 of the ABH system. Chem. Ber. 112, 3190-3202 (1979).
    • (1979) Chem. Ber , vol.112 , pp. 3190-3202
    • Paulsen, H.1    Kolar, C.2
  • 13
    • 0001924107 scopus 로고
    • The synthesis of derivatives of 3-0-(2-acetamido-2-deoxy-α-D galactopyranosyl)-L-serine and -L-threonine
    • Ferrari, B. & Pavia, A.A. The synthesis of derivatives of 3-0-(2-acetamido-2-deoxy-α-D galactopyranosyl)-L-serine and -L-threonine. Carbohydr. Res. 79, C1-C7 (1980).
    • (1980) Carbohydr. Res , vol.79
    • Ferrari, B.1    Pavia, A.A.2
  • 14
    • 0020210868 scopus 로고
    • Synthesis of the glycopeptide O beta-D-galactopyranosyl-(1 → 3) O (2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 → 3)-L-serine and -L-threonine
    • Paulsen, H. & Hölck, J. P. Synthesis of the glycopeptide O beta-D-galactopyranosyl-(1 → 3) O (2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 → 3)-L-serine and -L-threonine. Carbohydr. Res. 109, 89-107 (1982).
    • (1982) Carbohydr. Res , vol.109 , pp. 89-107
    • Paulsen, H.1    Hölck, J.P.2
  • 15
    • 84985257207 scopus 로고
    • Glycosyi imidates, 13. Application of the trichloroacetimidate procedure to 2-azidoglucose and 2-azidogalactose derivatives
    • Grundler, G. & Schmidt, R.R. Glycosyi imidates, 13. Application of the trichloroacetimidate procedure to 2-azidoglucose and 2-azidogalactose derivatives. Liebigs Ann. Chem. 1826-1847 (1994).
    • (1994) Liebigs Ann. Chem , vol.1826-1847
    • Grundler, G.1    Schmidt, R.R.2
  • 16
    • 0023373838 scopus 로고
    • Glycosylimidates. Part 24. Application of the trichloroacetimidate method to the synthesis of glycopeptides of the mucin type containing β-D-GaLp-(1 → 3)-D-GalpNAc unit
    • Kinzy, W. & Schmidt, R.R. Glycosylimidates. Part 24. Application of the trichloroacetimidate method to the synthesis of glycopeptides of the mucin type containing β-D-GaLp-(1 → 3)-D-GalpNAc unit. Carbohydr. Res. 164, 265-276 (1987).
    • (1987) Carbohydr. Res , vol.164 , pp. 265-276
    • Kinzy, W.1    Schmidt, R.R.2
  • 17
    • 84985261060 scopus 로고
    • Building units of oligosaccharides. Glycosidation of oligosaccharide thioglycosides to O-glycoprotein segments
    • Paulsen, H., Rauwald, W. & Weichert, U. Building units of oligosaccharides. Glycosidation of oligosaccharide thioglycosides to O-glycoprotein segments. Liebigs Ann. 75-86 (1988).
    • (1988) Liebigs Ann , vol.75-86
    • Paulsen, H.1    Rauwald, W.2    Weichert, U.3
  • 18
    • 0002297006 scopus 로고
    • Glycosylimidates. Part 39. Synthesis of glycopeptides of the mucin type containing a β-D-GlcpNAc-(1 → 3)-D-GalpNAc unit
    • Kinzy, W. & Schmidt, R.R. Glycosylimidates. Part 39. Synthesis of glycopeptides of the mucin type containing a β-D-GlcpNAc-(1 → 3)-D-GalpNAc unit. Carbohydr. Res. 193. 33-47 (1989).
    • (1989) Carbohydr. Res , vol.193 , pp. 33-47
    • Kinzy, W.1    Schmidt, R.R.2
  • 19
    • 0025168808 scopus 로고
    • Synthetic studies on cell surface glycans, 76. A highly stereoselective synthesis of di- and trimeric sialoxyl-Tn epitope: A partial structure of glycophorin A
    • Nakahara, Y.,Iijima, H., Sibayama, S. & Ogawa, T. Synthetic studies on cell surface glycans, 76. A highly stereoselective synthesis of di- and trimeric sialoxyl-Tn epitope: A partial structure of glycophorin A. Tetrahedron Lett. 31, 6897-6900 (1990).
    • (1990) Tetrahedron Lett , vol.31 , pp. 6897-6900
    • Nakahara, Y.1    Iijima, H.2    Sibayama, S.3    Ogawa, T.4
  • 20
    • 0028959305 scopus 로고
    • Solid-phase synthesis of a glycosylated hexapeptide of human sialophorin, using the trichloroacetimidate method
    • Rademann, J. & Schmidt, R.R. Solid-phase synthesis of a glycosylated hexapeptide of human sialophorin, using the trichloroacetimidate method. Carbohydr. Res. 269, 217-225 (1995).
    • (1995) Carbohydr. Res , vol.269 , pp. 217-225
    • Rademann, J.1    Schmidt, R.R.2
  • 21
    • 0032511367 scopus 로고    scopus 로고
    • Exploration of modalities in building α-O-linked systems through glycal assembly: A total synthesis of the mucin-related F1α antigen
    • Chen, X.T., Sames, D. & Danishefsky, S.J. Exploration of modalities in building α-O-linked systems through glycal assembly: A total synthesis of the mucin-related F1α antigen. J. Am. Chem. Soc. 120, 7760-7769 (1998).
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 7760-7769
    • Chen, X.T.1    Sames, D.2    Danishefsky, S.J.3
  • 22
    • 0035898445 scopus 로고    scopus 로고
    • Nitroglycal concatenation: A broadly applicable and efficient approach to the synthesis of complex O glycans
    • Winterfeld, G.A. & Schmidt, R.R. Nitroglycal concatenation: A broadly applicable and efficient approach to the synthesis of complex O glycans. Angew. Chem. Int. Ed. Engl. 40, 2654-2657 (2001).
    • (2001) Angew. Chem. Int. Ed. Engl , vol.40 , pp. 2654-2657
    • Winterfeld, G.A.1    Schmidt, R.R.2
  • 23
    • 0037353418 scopus 로고    scopus 로고
    • O-glycosyl amino acids by 2-nitrogalactal concatenation-synthesis of a mucin-type O glycan
    • Winterfeld, G.A., Khodair, A.I. & Schmidt, R.R. O-glycosyl amino acids by 2-nitrogalactal concatenation-synthesis of a mucin-type O glycan. Eur. J. Org. Chem. 6, 1009-1021 (2003).
    • (2003) Eur. J. Org. Chem , vol.6 , pp. 1009-1021
    • Winterfeld, G.A.1    Khodair, A.I.2    Schmidt, R.R.3
  • 24
    • 0038587670 scopus 로고    scopus 로고
    • Conjugate addition of phenols to 2-nitrogalactal-synthesis of O (2-acetamido-2-deoxygalactosyl)-tyrosine
    • Khodair, A.I., Winterfeld, G.A. & Schmidt, R.R. Conjugate addition of phenols to 2-nitrogalactal-synthesis of O (2-acetamido-2-deoxygalactosyl)-tyrosine. Eur. J. Org. Chem. 10, 1847-1852 (2003).
    • (2003) Eur. J. Org. Chem , vol.10 , pp. 1847-1852
    • Khodair, A.I.1    Winterfeld, G.A.2    Schmidt, R.R.3
  • 25
    • 34250178754 scopus 로고    scopus 로고
    • Glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis
    • Geiger, J. et al. Glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis, J. Org. Chem. 72, 4367-4377 (2007).
    • (2007) J. Org. Chem , vol.72 , pp. 4367-4377
    • Geiger, J.1
  • 26
    • 0002476872 scopus 로고    scopus 로고
    • Convenient glycoside synthesis of amino sugars. Michael-type addition to 2-nitro-D-galactal
    • Das, J. & Schmidt, R.R. Convenient glycoside synthesis of amino sugars. Michael-type addition to 2-nitro-D-galactal. Eur. J. Org. Chem. 8, 1609-1613 (1998).
    • (1998) Eur. J. Org. Chem , vol.8 , pp. 1609-1613
    • Das, J.1    Schmidt, R.R.2
  • 27
    • 2542632100 scopus 로고    scopus 로고
    • 2-Nitro thioglycoside donors: Versatile precursors of β-D glycosides of aminosugars
    • Barroca, N. & Schmidt, R.R. 2-Nitro thioglycoside donors: Versatile precursors of β-D glycosides of aminosugars. Org. Lett. 6, 1551-1554 (2004).
    • (2004) Org. Lett , vol.6 , pp. 1551-1554
    • Barroca, N.1    Schmidt, R.R.2
  • 28
    • 1942425168 scopus 로고    scopus 로고
    • Efficient methods for glycosidation with glycals - a key intermediate for the synthesis of mucin core 1-type O-glycan
    • Geiger, J., Barroca, N. & Schmidt, R.R. Efficient methods for glycosidation with glycals - a key intermediate for the synthesis of mucin core 1-type O-glycan. Synlett 5, 836-840 (2004).
    • (2004) Synlett , vol.5 , pp. 836-840
    • Geiger, J.1    Barroca, N.2    Schmidt, R.R.3
  • 29
    • 5444272571 scopus 로고    scopus 로고
    • Synthesis of glycosyl phosphonates by Michael-type addition to 2-nitroglycals
    • Pachamuthu, K., Figueroa-Perez, I., Ali, I.A.I. & Schmidt, R.R. Synthesis of glycosyl phosphonates by Michael-type addition to 2-nitroglycals. Eur. J. Org. Chem. 19, 3959-3961 (2004).
    • (2004) Eur. J. Org. Chem , vol.19 , pp. 3959-3961
    • Pachamuthu, K.1    Figueroa-Perez, I.2    Ali, I.A.I.3    Schmidt, R.R.4
  • 30
    • 0037623732 scopus 로고    scopus 로고
    • Diels-Alder reaction of 2-nitro glycals: A new route to the synthesis of benzopyrans
    • Pachamuthu, K. & Schmidt, R.R. Diels-Alder reaction of 2-nitro glycals: a new route to the synthesis of benzopyrans. Synlett 9, 1355-1357 (2003).
    • (2003) Synlett , vol.9 , pp. 1355-1357
    • Pachamuthu, K.1    Schmidt, R.R.2
  • 31
    • 0346057830 scopus 로고    scopus 로고
    • A convenient route to O glycosyl lactates via conjugate addition to 2-nitroglycals: Ring closure to novel pyrano[2.3-b][1,4]-oxazines
    • Khodair, A.I., Pachamuthu, K. & Schmidt, R.R. A convenient route to O glycosyl lactates via conjugate addition to 2-nitroglycals: Ring closure to novel pyrano[2.3-b][1,4]-oxazines. Synthesis 1, 53-58 (2004).
    • (2004) Synthesis , vol.1 , pp. 53-58
    • Khodair, A.I.1    Pachamuthu, K.2    Schmidt, R.R.3
  • 32
    • 0036090891 scopus 로고    scopus 로고
    • An easy route to 2-amino β-C-glycosides by conjugate addition to 2-nitroglycals
    • Pachamuthu, K., Gupta, A., Das, J., Schmidt, R.R. & Vankar, Y.D. An easy route to 2-amino β-C-glycosides by conjugate addition to 2-nitroglycals. Eur. J. Org. Chem. 9, 1479-1483 (2002).
    • (2002) Eur. J. Org. Chem , vol.9 , pp. 1479-1483
    • Pachamuthu, K.1    Gupta, A.2    Das, J.3    Schmidt, R.R.4    Vankar, Y.D.5
  • 33
    • 0033816663 scopus 로고    scopus 로고
    • Convenient synthesis of nucleosides of 2-deoxy-2-nitro-D-galactose and N-acetyl-D-galactosamine
    • Winterfeld, G.A., Das, J. & Schmidt, R.R. Convenient synthesis of nucleosides of 2-deoxy-2-nitro-D-galactose and N-acetyl-D-galactosamine. Eur. J. Org. Chem. 17, 3047-3050 (2000).
    • (2000) Eur. J. Org. Chem , vol.17 , pp. 3047-3050
    • Winterfeld, G.A.1    Das, J.2    Schmidt, R.R.3
  • 34
    • 16844373916 scopus 로고    scopus 로고
    • The synthesis of hybrids of D-galactose with 1-deoxynojirimycin analogs as glycosidase inhibitors
    • Reddy, B.G. & Vankar, Y.D. The synthesis of hybrids of D-galactose with 1-deoxynojirimycin analogs as glycosidase inhibitors. Angew. Chem. Int. Ed. Engl. 44, 2001-2004 (2005).
    • (2005) Angew. Chem. Int. Ed. Engl , vol.44 , pp. 2001-2004
    • Reddy, B.G.1    Vankar, Y.D.2
  • 35
    • 33750444958 scopus 로고    scopus 로고
    • Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids
    • Jayakanthan, K. & Vankar, Y.D. Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids. Tetrahedron Lett. 47, 8667-8671 (2006).
    • (2006) Tetrahedron Lett , vol.47 , pp. 8667-8671
    • Jayakanthan, K.1    Vankar, Y.D.2
  • 37
    • 0025279248 scopus 로고
    • Synthetic studies on plant cell wall glycans. Part 8. Total synthesis of nonasaccharide repeating unit of plant cell wall xyloglucan: An endogenous hormone which regulates cell growth
    • Sakai, K., Nakahara, Y. & Ogawa, T. Synthetic studies on plant cell wall glycans. Part 8. Total synthesis of nonasaccharide repeating unit of plant cell wall xyloglucan: An endogenous hormone which regulates cell growth. Tetrahedron Lett. 31, 3035-3038 (1990).
    • (1990) Tetrahedron Lett , vol.31 , pp. 3035-3038
    • Sakai, K.1    Nakahara, Y.2    Ogawa, T.3
  • 38
    • 0025191224 scopus 로고
    • Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane
    • Oppolzer, W. & Tamura, O. Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane. Tetrahedron Lett. 31, 991-994 (1990).
    • (1990) Tetrahedron Lett , vol.31 , pp. 991-994
    • Oppolzer, W.1    Tamura, O.2
  • 39
    • 0037275422 scopus 로고    scopus 로고
    • Hydrazinium monoformate: A new hydrogen donor. Selective reduction of nitro compounds catalyzed by commercial zinc dust
    • Gowda, S., Gowda, B.K.K. & Gowda, D.C. Hydrazinium monoformate: A new hydrogen donor. Selective reduction of nitro compounds catalyzed by commercial zinc dust. Synth. Commun. 33, 281-289 (2003).
    • (2003) Synth. Commun , vol.33 , pp. 281-289
    • Gowda, S.1    Gowda, B.K.K.2    Gowda, D.C.3
  • 40
    • 38349142889 scopus 로고    scopus 로고
    • Nishimura, S. Raney nickel and platinized Raney nickel with higher catalytic activities. Bull. Chem. Soc. Jpn. 32, 61-64 (1959).
    • Nishimura, S. Raney nickel and platinized Raney nickel with higher catalytic activities. Bull. Chem. Soc. Jpn. 32, 61-64 (1959).
  • 41
    • 38349111823 scopus 로고    scopus 로고
    • Geiger, J. Dissertation, Synthese von Mucin-Tyn Core-Strukturen und Antifreeze-Glycoproteinfragmenten, Universität Konstanz, 2005 (Hartung-Gorre Verlag, Konstanz, Germany, 2005).
    • Geiger, J. Dissertation, Synthese von Mucin-Tyn Core-Strukturen und Antifreeze-Glycoproteinfragmenten, Universität Konstanz, 2005 (Hartung-Gorre Verlag, Konstanz, Germany, 2005).


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