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Volumn 5, Issue 9, 2013, Pages 790-795

Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BIOLOGICAL PRODUCT; MONOSACCHARIDE;

EID: 84883144319     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1726     Document Type: Article
Times cited : (121)

References (51)
  • 2
    • 44249098800 scopus 로고    scopus 로고
    • Natural products to drugs: Natural product-derived compounds in clinical trials
    • Butler, M. S. Natural products to drugs: natural product-derived compounds in clinical trials. Nat. Prod. Rep. 25, 475-516 (2008).
    • (2008) Nat. Prod. Rep. , vol.25 , pp. 475-516
    • Butler, M.S.1
  • 3
    • 44049095632 scopus 로고    scopus 로고
    • Protein-glycan interactions in the control of innate and adaptive immune responses
    • van Kooyk, Y. & Rabinovich, G. A. Protein-glycan interactions in the control of innate and adaptive immune responses. Nature Immunol. 9, 593-601 (2008).
    • (2008) Nature Immunol. , vol.9 , pp. 593-601
    • Van Kooyk, Y.1    Rabinovich, G.A.2
  • 4
    • 0035937505 scopus 로고    scopus 로고
    • Intracellular functions of N-linked glycans
    • Helenius, A. & Aebi, M. Intracellular functions of N-linked glycans. Science 291, 2364-2369 (2001).
    • (2001) Science , vol.291 , pp. 2364-2369
    • Helenius, A.1    Aebi, M.2
  • 5
    • 0031127564 scopus 로고    scopus 로고
    • The role of carbohydrates in biologically active natural products
    • Weymouth-Wilson, A. C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 14, 99-110 (1997).
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 99-110
    • Weymouth-Wilson, A.C.1
  • 6
    • 79952033077 scopus 로고    scopus 로고
    • Natural glycoconjugates with antitumor activity
    • La Ferla, B. et al. Natural glycoconjugates with antitumor activity. Nat. Prod. Rep. 28, 630-648 (2011).
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 630-648
    • La Ferla, B.1
  • 7
    • 26044440288 scopus 로고    scopus 로고
    • Automated synthesis of oligosaccharides as a basis for drug discovery
    • Seeberger, P. H. & Werz, D. B. Automated synthesis of oligosaccharides as a basis for drug discovery. Nature Rev. Drug. Discov. 4, 751-763 (2005).
    • (2005) Nature Rev. Drug. Discov. , vol.4 , pp. 751-763
    • Seeberger, P.H.1    Werz, D.B.2
  • 8
    • 61849111654 scopus 로고    scopus 로고
    • New principles for glycoside-bond formation
    • Zhu, X. & Schmidt, R. R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. 48, 1900-1934 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1900-1934
    • Zhu, X.1    Schmidt, R.R.2
  • 10
    • 84867080246 scopus 로고    scopus 로고
    • Solving the convergence problem in the synthesis of triantennary N-glycan relevant to prostate-specific membrane antigen (PSMA)
    • Walczak, M. A. & Danishefsky, S. J. Solving the convergence problem in the synthesis of triantennary N-glycan relevant to prostate-specific membrane antigen (PSMA). J. Am. Chem. Soc. 134, 16430-16433 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 16430-16433
    • Walczak, M.A.1    Danishefsky, S.J.2
  • 11
    • 0015927426 scopus 로고
    • Remote oxidation of steroids by photolysis of attached benzophenone groups
    • Breslow, R. et al. Remote oxidation of steroids by photolysis of attached benzophenone groups. J. Am. Chem. Soc. 95, 3251-3262 (1973).
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3251-3262
    • Breslow, R.1
  • 12
    • 0017764981 scopus 로고
    • Selective halogenation of steroids using attached aryl iodide templates
    • Breslow, R. et al. Selective halogenation of steroids using attached aryl iodide templates. J. Am. Chem. Soc. 99, 905-915 (1977).
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 905-915
    • Breslow, R.1
  • 13
    • 33845553152 scopus 로고
    • Catalytic multiple template-directed steroid chlorinations
    • Breslow, R. & Heyer, D. Catalytic multiple template-directed steroid chlorinations. J. Am. Chem. Soc. 104, 2045-2046 (1982).
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2045-2046
    • Breslow, R.1    Heyer, D.2
  • 14
    • 33748581386 scopus 로고    scopus 로고
    • Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts
    • Lewis, C. A. & Miller, S. J. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts. Angew. Chem. Int. Ed. 45, 5616-5619 (2006).
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5616-5619
    • Lewis, C.A.1    Miller, S.J.2
  • 15
    • 40949096433 scopus 로고    scopus 로고
    • A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
    • Chen, M. S. & White, M. C. A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science 318, 783-787 (2007).
    • (2007) Science , vol.318 , pp. 783-787
    • Chen, M.S.1    White, M.C.2
  • 16
    • 77955848701 scopus 로고    scopus 로고
    • Perfectly regioselective acylation of a cardiac glycoside, digitoxin, via catalytic amplification of the intrinsic reactivity
    • Yoshida, K., Furuta, T. & Kawabata, T. Perfectly regioselective acylation of a cardiac glycoside, digitoxin, via catalytic amplification of the intrinsic reactivity. Tetrahedron Lett. 51, 4830-4832 (2010).
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4830-4832
    • Yoshida, K.1    Furuta, T.2    Kawabata, T.3
  • 17
    • 79959554069 scopus 로고    scopus 로고
    • Regioselective reactions for programmable resveratrol oligomer synthesis
    • Snyder, S. A., Gollner, A. & Chiriac, M. I. Regioselective reactions for programmable resveratrol oligomer synthesis. Nature 474, 461-466 (2011).
    • (2011) Nature , vol.474 , pp. 461-466
    • Snyder, S.A.1    Gollner, A.2    Chiriac, M.I.3
  • 19
    • 84859592619 scopus 로고    scopus 로고
    • Site-selective bromination of vancomycin
    • Pathak, T. P. & Miller, S. J. Site-selective bromination of vancomycin. J. Am. Chem. Soc. 134, 6120-6123 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 6120-6123
    • Pathak, T.P.1    Miller, S.J.2
  • 20
    • 84870201767 scopus 로고    scopus 로고
    • Electronic tuning of site-selectivity
    • Wilcock, B. C. et al. Electronic tuning of site-selectivity. Nature Chem. 4, 996-1003 (2012).
    • (2012) Nature Chem. , vol.4 , pp. 996-1003
    • Wilcock, B.C.1
  • 21
    • 84862168336 scopus 로고    scopus 로고
    • Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects
    • Fowler, B. S., Laemmerhold, K. M. & Miller, S. J. Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects. J. Am. Chem. Soc. 134, 9755-9761 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 9755-9761
    • Fowler, B.S.1    Laemmerhold, K.M.2    Miller, S.J.3
  • 22
    • 84875134430 scopus 로고    scopus 로고
    • Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin
    • Beale, T. M. & Taylor, M. S. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org. Lett. 15, 1358-1361 (2013).
    • (2013) Org. Lett. , vol.15 , pp. 1358-1361
    • Beale, T.M.1    Taylor, M.S.2
  • 23
    • 84878634623 scopus 로고    scopus 로고
    • Chemical tailoring of teicoplanin with site-selective reactions
    • Pathak, T. P. & Miller, S. J. Chemical tailoring of teicoplanin with site-selective reactions. J. Am. Chem. Soc. 135, 8415-8422 (2013).
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 8415-8422
    • Pathak, T.P.1    Miller, S.J.2
  • 24
    • 84868618354 scopus 로고    scopus 로고
    • Catalyst-controlled regioselective reactions of carbohydrate derivatives
    • Lee, D. & Taylor, M. S. Catalyst-controlled regioselective reactions of carbohydrate derivatives. Synthesis 44, 3421-3431 (2012).
    • (2012) Synthesis , vol.44 , pp. 3421-3431
    • Lee, D.1    Taylor, M.S.2
  • 25
    • 35549002267 scopus 로고    scopus 로고
    • A catalytic one-step process for the chemo-and regioselective acylation of monosaccharides
    • Kawabata, T., Muramatsu, W., Nishio, T., Shibata, T. & Schedel, H. A catalytic one-step process for the chemo-and regioselective acylation of monosaccharides. J. Am. Chem. Soc. 129, 12890-12895 (2007).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12890-12895
    • Kawabata, T.1    Muramatsu, W.2    Nishio, T.3    Shibata, T.4    Schedel, H.5
  • 26
    • 67650487533 scopus 로고    scopus 로고
    • Nonenzymatic regioselective acylation of carbohydrates
    • Kawabata, T. & Furuta, T. Nonenzymatic regioselective acylation of carbohydrates. Chem. Lett. 38, 640-647 (2009).
    • (2009) Chem. Lett. , vol.38 , pp. 640-647
    • Kawabata, T.1    Furuta, T.2
  • 27
    • 0142217515 scopus 로고    scopus 로고
    • A peptide-based catalyst approach to regioselective functionalization of carbohydrates
    • Griswold, K. S. & Miller, S. J. A peptide-based catalyst approach to regioselective functionalization of carbohydrates. Tetrahedron 59, 8869-8875 (2003).
    • (2003) Tetrahedron , vol.59 , pp. 8869-8875
    • Griswold, K.S.1    Miller, S.J.2
  • 28
    • 80052323742 scopus 로고    scopus 로고
    • Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst
    • Gouliaras, C., Lee, D., Chan, L. & Taylor, M. S. Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst. J. Am. Chem. Soc. 133, 13926-13929 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13926-13929
    • Gouliaras, C.1    Lee, D.2    Chan, L.3    Taylor, M.S.4
  • 29
    • 79958845198 scopus 로고    scopus 로고
    • Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative
    • Chan, L. & Taylor, M. S. Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative. Org. Lett. 13, 3090-3093 (2011).
    • (2011) Org. Lett. , vol.13 , pp. 3090-3093
    • Chan, L.1    Taylor, M.S.2
  • 30
    • 79952765683 scopus 로고    scopus 로고
    • Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives
    • Lee, D. & Taylor, M. S. Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives. J. Am. Chem. Soc. 133, 3724-3727 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 3724-3727
    • Lee, D.1    Taylor, M.S.2
  • 31
    • 84862068667 scopus 로고    scopus 로고
    • Borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: Expansion of substrate scope and mechanistic studies
    • Lee, D., Williamson, C. L., Chan, L. & Taylor, M. S. Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: expansion of substrate scope and mechanistic studies. J. Am. Chem. Soc. 134, 8260-8267 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 8260-8267
    • Lee, D.1    Williamson, C.L.2    Chan, L.3    Regioselective, S.T.M.4
  • 32
    • 0036962906 scopus 로고    scopus 로고
    • Regioselective benzoylation of 6-O-protected and 4, 6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1, 2-diamines
    • Hu, G. & Vasella, A. Regioselective benzoylation of 6-O-protected and 4, 6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1, 2-diamines. Helv. Chim. Acta 85, 4369-4391 (2002).
    • (2002) Helv. Chim. Acta , vol.85 , pp. 4369-4391
    • Hu, G.1    Vasella, A.2
  • 33
    • 0015101706 scopus 로고
    • Entropic contributions to rate accelerations in enzymic and intramolecular reactions and chelate effect
    • Page, M. I. & Jencks, W. P. Entropic contributions to rate accelerations in enzymic and intramolecular reactions and chelate effect. Proc. Natl Acad. Sci. USA 68, 1678-1683 (1971).
    • (1971) Proc. Natl Acad. Sci. USA , vol.68 , pp. 1678-1683
    • Page, M.I.1    Jencks, W.P.2
  • 34
    • 2342420346 scopus 로고    scopus 로고
    • Structure of Kre2p/Mnt1p: A yeast a 1, 2-mannosyltransferase involved in mannoprotein biosynthesis
    • Lobsanov, Y. D. et al. Structure of Kre2p/Mnt1p: a yeast a 1, 2-mannosyltransferase involved in mannoprotein biosynthesis. J. Biol. Chem. 279, 17921-17931 (2004).
    • (2004) J. Biol. Chem. , vol.279 , pp. 17921-17931
    • Lobsanov, Y.D.1
  • 35
    • 80051776167 scopus 로고    scopus 로고
    • Scaffolding catalysts: Highly enantioselective desymmetrization reactions
    • Sun, X., Worthy, A. D. & Tan, K. L. Scaffolding catalysts: highly enantioselective desymmetrization reactions. Angew. Chem. Int. Ed. 50, 8167-8171 (2011).
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8167-8171
    • Sun, X.1    Worthy, A.D.2    Tan, K.L.3
  • 36
    • 84860817719 scopus 로고    scopus 로고
    • Site-selective catalysis: Toward a regiodivergent resolution of 1, 2-diols
    • Worthy, A. D., Sun, X. & Tan, K. L. Site-selective catalysis: toward a regiodivergent resolution of 1, 2-diols. J. Am. Chem. Soc. 134, 7321-7324 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 7321-7324
    • Worthy, A.D.1    Sun, X.2    Tan, K.L.3
  • 37
    • 33748413162 scopus 로고    scopus 로고
    • Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule
    • Zhao, Y., Rodrigo, J., Hoveyda, A. H. & Snapper, M. L. Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule. Nature 443, 67-70 (2006).
    • (2006) Nature , vol.443 , pp. 67-70
    • Zhao, Y.1    Rodrigo, J.2    Hoveyda, A.H.3    Snapper, M.L.4
  • 38
    • 0035819659 scopus 로고    scopus 로고
    • Modified guanidines as chiral superbases: The first example of asymmetric silylation of secondary alcohols
    • Isobe, T., Fukuda, K., Araki, Y. & Ishikawa, T. Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols. Chem. Commun. 7, 243-244 (2001).
    • (2001) Chem. Commun. , vol.7 , pp. 243-244
    • Isobe, T.1    Fukuda, K.2    Araki, Y.3    Ishikawa, T.4
  • 40
    • 36148978554 scopus 로고    scopus 로고
    • Kinetic resolution of 1, 2-diols through highly site-and enantioselective catalytic silylation
    • Zhao, Y., Mitra, A. W., Hoveyda, A. H. & Snapper, M. L. Kinetic resolution of 1, 2-diols through highly site-and enantioselective catalytic silylation. Angew. Chem. Int. Ed. 46, 8471-8474 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8471-8474
    • Zhao, Y.1    Mitra, A.W.2    Hoveyda, A.H.3    Snapper, M.L.4
  • 41
    • 79961071823 scopus 로고    scopus 로고
    • Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A
    • Rodrigo, J. M., Zhao, Y., Hoveyda, A. H. & Snapper, M. L. Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A. Org. Lett. 13, 3778-3781 (2011).
    • (2011) Org. Lett. , vol.13 , pp. 3778-3781
    • Rodrigo, J.M.1    Zhao, Y.2    Hoveyda, A.H.3    Snapper, M.L.4
  • 42
    • 79961057514 scopus 로고    scopus 로고
    • Silylation-based kinetic resolution of monofunctional secondary alcohols
    • Sheppard, C. I., Taylor, J. L. & Wiskur, S. L. Silylation-based kinetic resolution of monofunctional secondary alcohols. Org. Lett. 13, 3794-3797 (2011).
    • (2011) Org. Lett. , vol.13 , pp. 3794-3797
    • Sheppard, C.I.1    Taylor, J.L.2    Wiskur, S.L.3
  • 43
    • 84859553203 scopus 로고    scopus 로고
    • Catalytic enantioselective dehydrogenative Si-O coupling of oxime ether-functionalized alcohols
    • Weickgenannt, A., Mohr, J. & Oestreich, M. Catalytic enantioselective dehydrogenative Si-O coupling of oxime ether-functionalized alcohols. Tetrahedron 68, 3468-3479 (2012).
    • (2012) Tetrahedron , vol.68 , pp. 3468-3479
    • Weickgenannt, A.1    Mohr, J.2    Oestreich, M.3
  • 44
    • 0037573574 scopus 로고    scopus 로고
    • Catalysis through induced intramolecularity: What can be learned by mimicking enzymes with carbonyl compounds that covalently bind substrates?
    • Pascal, R. Catalysis through induced intramolecularity: what can be learned by mimicking enzymes with carbonyl compounds that covalently bind substrates? Eur. J. Org. Chem., 10, 1813-1824 (2003).
    • (2003) Eur. J. Org. Chem. , vol.10 , pp. 1813-1824
    • Pascal, R.1
  • 45
    • 79961244115 scopus 로고    scopus 로고
    • Induced intramolecularity: An effective strategy in catalysis
    • Tan, K. L. Induced intramolecularity: an effective strategy in catalysis. ACS Cat. 1, 877-886 (2011).
    • (2011) ACS Cat. , vol.1 , pp. 877-886
    • Tan, K.L.1
  • 46
    • 84867366871 scopus 로고    scopus 로고
    • Catalysis through temporary intramolecularity: Mechanistic investigations on aldehyde-catalyzed Cope-type hydroamination lead to the discovery of a more efficient tethering catalyst
    • Guimond, N., MacDonald, M. J., Lemieux, V. & Beauchemin, A. M. Catalysis through temporary intramolecularity: mechanistic investigations on aldehyde-catalyzed Cope-type hydroamination lead to the discovery of a more efficient tethering catalyst. J. Am. Chem. Soc. 134, 16571-16577 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 16571-16577
    • Guimond, N.1    MacDonald, M.J.2    Lemieux, V.3    Beauchemin, A.M.4
  • 47
    • 84873632774 scopus 로고    scopus 로고
    • Highly enantioselective intermolecular hydroamination of allylic amines with chiral aldehydes as tethering catalysts
    • MacDonald, M. J., Hesp, C. R., Schipper, D. J., Pesant, M. & Beauchemin, A. M. Highly enantioselective intermolecular hydroamination of allylic amines with chiral aldehydes as tethering catalysts. Chem. Eur. J. 19, 2597-2601 (2013).
    • (2013) Chem. Eur. J. , vol.19 , pp. 2597-2601
    • MacDonald, M.J.1    Hesp, C.R.2    Schipper, D.J.3    Pesant, M.4    Beauchemin, A.M.5
  • 48
    • 56549100977 scopus 로고    scopus 로고
    • Protecting groups for RNA synthesis: An increasing need for selective preparative methods
    • Somoza, A. Protecting groups for RNA synthesis: an increasing need for selective preparative methods. Chem. Soc. Rev. 37, 2668-2675 (2008).
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 2668-2675
    • Somoza, A.1
  • 49
    • 0030669282 scopus 로고    scopus 로고
    • Status and prospect of current inotropic agents
    • Repke, K. R. H. & Megges, R. Status and prospect of current inotropic agents. Expert Opin. Ther. Pat. 7, 1297-1306 (1997).
    • (1997) Expert Opin. Ther. Pat. , vol.7 , pp. 1297-1306
    • Repke, K.R.H.1    Megges, R.2
  • 51
    • 0033551859 scopus 로고    scopus 로고
    • Insights into editing from an Ile-tRNA synthetase structure with tRNA(Ile) and mupirocin
    • Silvian, L. F., Wang, J. & Steitz, T. A. Insights into editing from an Ile-tRNA synthetase structure with tRNA(Ile) and mupirocin. Science 285, 1074-1077 (1999).
    • (1999) Science , vol.285 , pp. 1074-1077
    • Silvian, L.F.1    Wang, J.2    Steitz, T.A.3


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