Tin(IV) catalyzed D-galacturonic acid anomerization (312 views visite)
Dalton T (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2008 Feb 7; (5): 596-601.
Export to Esporta in BibTeX Export to Esporta in EndNote
Paper type Tipo di articolo: Journal Article,
Impact factor: 3.58, 5-year impact factor Impact factor a 5 anni: 3.409
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-38549175678&partnerID=40&md5=3db2ef887ed56752e0b03829fb72c65c
Keywords Parole chiave: Aldehydes, Catalysis, Enthalpy, Ligands, Nucleophiles, Anomerization, Carboxylic Tail, Galacturonic Acid, Mutarotation Rate Profiles, Nucleophilic Attack, Reaction Kinetics, Hexuronic Acid, Tin Derivative, Article, Chemistry, Nuclear Magnetic Resonance Spectroscopy, Stereoisomerism, Tin Compounds,
Affiliations Affiliazioni:
*** IBB - CNR ***
Dipartimento CICACF, Università di Messina-Salita Sperone, 31-98166 S.Agata-Messina, Italy
Dipartimento di Chimica Inorganica e Analitica, Università di Palermo, Viale delle Scienze Parco D'Orleans II, I-90123 Palermo, Italy
IBB-CNR Catania, via A. Doria 6, 95125-Catania, Italy
Dipartimento CICACF-Universita di Messina-Salita Sperone, 31-98166 S.Agata-Messina, Italy. arotondo@unime.it,
References Riferimenti:
Angyal, S.J., (1980) Chem. Soc. Rev., 9, p. 41
Verchere, J.-F., Chapelle, S., Xin, F., Crans, D.C., (1998) Prog. Inorg. Chem., 47, p. 837
Parulli, U., Floriani, C., (1997) Prog. Inorg. Chem., 45, p. 393. , -429
Brett, C.T., Waldron, K.W., (1990) The Physiology and Biochemistry of Plant Cell Wall, Ed., , Unwin Hyman, Chapman & Hall, London
Ramamoorthy, S., Leppard, G.G., (1977) J. Theor. Biol., 66 (3), p. 527
Tang -. H, R., Belton, P.S., Davies, S.C., Hughes, D.L., (2001) Carbohydr. Res., 330 (3), p. 391
Brown, W.H., Foote, C.S., (1998) Organic Chemistry, , Saunders College Publishing, Orlando, Florida, USA, 2nd edn
Angyal, S.J., (1991) Adv. Carbohydr. Chem. Biochem., 49, p. 20
Brønsted, J.N., Guggenheim, E.A., (1927) J. Am. Chem. Soc., 49, p. 2554
Ryu, K.-S., Kim, C., Kim, I., Yoo, S., Choi, B.-S., Park, C., (2004) J. Biol. Chem., 279 (24), p. 25544. , -25548
Sehray, K.J., Benkovic, S.J., (1978) Acc. Chem. Res., 2, p. 136. , -141
Sneyder, G.R., Serianni, A.S., (1991) Carbohydr. Res., 210, p. 21. , -38
Anderson, L., Garver, J.C., Computer Modeling of the Kinetic of Tautomerization (Mutarotation) of aldoses: Implications for the Mechanism of the Process in (1973) Carbohydrates in Solution, Advances in Chemistry, Series, 117, Ed., , R. Gould, American Chemical Society, Washington D.C., p. 20
Bertazzi, N., Bruschetta, G., Casella, G., Pellerito, L., Rotondo, E., Scopelliti, M., (2003) Appl. Organomet. Chem., 17, p. 932. , -939
Ramos, M.L., Caldeira, M.M., Gil, V.M.S., (1997) Carbohydr. Res., 297 (3), p. 191. , -200
Capon, B., (1969) Chem. Rev., 69 (4), p. 407. , -498
Capon, B., Walker, R.B., (1974) J. Chem. Soc., Perkin Trans. 2, p. 1600. , -1610
Swain, C.G., (1950) J. Am. Chem. Soc., 72, p. 4578. , -4583
Swain, C.G., Brown, J.F., (1952) J. Am. Chem. Soc., 74, p. 2534. , -2538
O'Connor, C.J., Odell, A.L., Bailey, A.T., (1983) Aust. J. Chem., 36, p. 279. , -287
Beebe, J.A., Arabshahi, A., Clifton, J.G., Ringe, D., Petsko, G.A., Frey, P.A., (2003) Biochemistry, 42, p. 4414. , -4420
Nowacki, A., Smiatoczova, K., Kasprzykowska, R., Domochowska, B., Wisniewski, A., (2002) Carbohydr. Res., 337, p. 265. , -272
Isbell, H.S., Frush, H.L., Wade, C.W.R., Hunter, C.E., (1969) Carbohydr. Res., 9, p. 163. , -175
Serianni, A.S., Pierce, J., Huang, S.-G., Barker, R., (1982) J. Am. Chem. Soc., 15, p. 4037. , -4044
Ernst, R.R., Bodenhausen, G., Wokaun, A., (1990) Principles of Nuclear Magnetic Resonance, , Oxford Science Publications, Oxford, UK
Zolnai, Z., Juranic, N., Vikic-Topic, D., MacUra, S., (2000) J. Chem. Inf. Comput. Sci., 40, p. 611
Cobas, J.C., Martin-Pastor, M., (2004) EXSY Calc, Version 1.0, ©, , Mestrec, Universidad de Santiago de Compostela, Spain
Sandstrom, J., (1982) Dynamic NMR Spectroscopy, , Academic Press Inc. Ltd, London, pp. 80-81
Budzelaar, P.H.M., (1995) G-NMR, Version 4.0, , Cherwell Scientific Publishing, Palo Alto, CA, USA, ©
Angyal, S. J., (1980) Chem. Soc. Rev., 9, p. 41
Verchere, J. -F., Chapelle, S., Xin, F., Crans, D. C., (1998) Prog. Inorg. Chem., 47, p. 837
Brett, C. T., Waldron, K. W., (1990) The Physiology and Biochemistry of Plant Cell Wall, Ed., , Unwin Hyman, Chapman & Hall, London
Brown, W. H., Foote, C. S., (1998) Organic Chemistry, , Saunders College Publishing, Orlando, Florida, USA, 2nd edn
Angyal, S. J., (1991) Adv. Carbohydr. Chem. Biochem., 49, p. 20
Br nsted, J. N., Guggenheim, E. A., (1927) J. Am. Chem. Soc., 49, p. 2554
Ryu, K. -S., Kim, C., Kim, I., Yoo, S., Choi, B. -S., Park, C., (2004) J. Biol. Chem., 279 (24), p. 25544. , -25548
Sehray, K. J., Benkovic, S. J., (1978) Acc. Chem. Res., 2, p. 136. , -141
Sneyder, G. R., Serianni, A. S., (1991) Carbohydr. Res., 210, p. 21. , -38
Ramos, M. L., Caldeira, M. M., Gil, V. M. S., (1997) Carbohydr. Res., 297 (3), p. 191. , -200
Swain, C. G., (1950) J. Am. Chem. Soc., 72, p. 4578. , -4583
Swain, C. G., Brown, J. F., (1952) J. Am. Chem. Soc., 74, p. 2534. , -2538
O'Connor, C. J., Odell, A. L., Bailey, A. T., (1983) Aust. J. Chem., 36, p. 279. , -287
Beebe, J. A., Arabshahi, A., Clifton, J. G., Ringe, D., Petsko, G. A., Frey, P. A., (2003) Biochemistry, 42, p. 4414. , -4420
Isbell, H. S., Frush, H. L., Wade, C. W. R., Hunter, C. E., (1969) Carbohydr. Res., 9, p. 163. , -175
Serianni, A. S., Pierce, J., Huang, S. -G., Barker, R., (1982) J. Am. Chem. Soc., 15, p. 4037. , -4044
Ernst, R. R., Bodenhausen, G., Wokaun, A., (1990) Principles of Nuclear Magnetic Resonance, , Oxford Science Publications, Oxford, UK
Cobas, J. C., Martin-Pastor, M., (2004) EXSY Calc, Version 1. 0, , , Mestrec, Universidad de Santiago de Compostela, Spain
Budzelaar, P. H. M., (1995) G-NMR, Version 4. 0, , Cherwell Scientific Publishing, Palo Alto, CA, USA,
Dalton T (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2008 Feb 7; (5): 596-601.
Export to Esporta in BibTeX Export to Esporta in EndNote
Paper type Tipo di articolo: Journal Article,
Impact factor: 3.58, 5-year impact factor Impact factor a 5 anni: 3.409
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-38549175678&partnerID=40&md5=3db2ef887ed56752e0b03829fb72c65c
Keywords Parole chiave: Aldehydes, Catalysis, Enthalpy, Ligands, Nucleophiles, Anomerization, Carboxylic Tail, Galacturonic Acid, Mutarotation Rate Profiles, Nucleophilic Attack, Reaction Kinetics, Hexuronic Acid, Tin Derivative, Article, Chemistry, Nuclear Magnetic Resonance Spectroscopy, Stereoisomerism, Tin Compounds,
Affiliations Affiliazioni:
*** IBB - CNR ***
Dipartimento CICACF, Università di Messina-Salita Sperone, 31-98166 S.Agata-Messina, Italy
Dipartimento di Chimica Inorganica e Analitica, Università di Palermo, Viale delle Scienze Parco D'Orleans II, I-90123 Palermo, Italy
IBB-CNR Catania, via A. Doria 6, 95125-Catania, Italy
Dipartimento CICACF-Universita di Messina-Salita Sperone, 31-98166 S.Agata-Messina, Italy. arotondo@unime.it,
References Riferimenti:
Angyal, S.J., (1980) Chem. Soc. Rev., 9, p. 41
Verchere, J.-F., Chapelle, S., Xin, F., Crans, D.C., (1998) Prog. Inorg. Chem., 47, p. 837
Parulli, U., Floriani, C., (1997) Prog. Inorg. Chem., 45, p. 393. , -429
Brett, C.T., Waldron, K.W., (1990) The Physiology and Biochemistry of Plant Cell Wall, Ed., , Unwin Hyman, Chapman & Hall, London
Ramamoorthy, S., Leppard, G.G., (1977) J. Theor. Biol., 66 (3), p. 527
Tang -. H, R., Belton, P.S., Davies, S.C., Hughes, D.L., (2001) Carbohydr. Res., 330 (3), p. 391
Brown, W.H., Foote, C.S., (1998) Organic Chemistry, , Saunders College Publishing, Orlando, Florida, USA, 2nd edn
Angyal, S.J., (1991) Adv. Carbohydr. Chem. Biochem., 49, p. 20
Brønsted, J.N., Guggenheim, E.A., (1927) J. Am. Chem. Soc., 49, p. 2554
Ryu, K.-S., Kim, C., Kim, I., Yoo, S., Choi, B.-S., Park, C., (2004) J. Biol. Chem., 279 (24), p. 25544. , -25548
Sehray, K.J., Benkovic, S.J., (1978) Acc. Chem. Res., 2, p. 136. , -141
Sneyder, G.R., Serianni, A.S., (1991) Carbohydr. Res., 210, p. 21. , -38
Anderson, L., Garver, J.C., Computer Modeling of the Kinetic of Tautomerization (Mutarotation) of aldoses: Implications for the Mechanism of the Process in (1973) Carbohydrates in Solution, Advances in Chemistry, Series, 117, Ed., , R. Gould, American Chemical Society, Washington D.C., p. 20
Bertazzi, N., Bruschetta, G., Casella, G., Pellerito, L., Rotondo, E., Scopelliti, M., (2003) Appl. Organomet. Chem., 17, p. 932. , -939
Ramos, M.L., Caldeira, M.M., Gil, V.M.S., (1997) Carbohydr. Res., 297 (3), p. 191. , -200
Capon, B., (1969) Chem. Rev., 69 (4), p. 407. , -498
Capon, B., Walker, R.B., (1974) J. Chem. Soc., Perkin Trans. 2, p. 1600. , -1610
Swain, C.G., (1950) J. Am. Chem. Soc., 72, p. 4578. , -4583
Swain, C.G., Brown, J.F., (1952) J. Am. Chem. Soc., 74, p. 2534. , -2538
O'Connor, C.J., Odell, A.L., Bailey, A.T., (1983) Aust. J. Chem., 36, p. 279. , -287
Beebe, J.A., Arabshahi, A., Clifton, J.G., Ringe, D., Petsko, G.A., Frey, P.A., (2003) Biochemistry, 42, p. 4414. , -4420
Nowacki, A., Smiatoczova, K., Kasprzykowska, R., Domochowska, B., Wisniewski, A., (2002) Carbohydr. Res., 337, p. 265. , -272
Isbell, H.S., Frush, H.L., Wade, C.W.R., Hunter, C.E., (1969) Carbohydr. Res., 9, p. 163. , -175
Serianni, A.S., Pierce, J., Huang, S.-G., Barker, R., (1982) J. Am. Chem. Soc., 15, p. 4037. , -4044
Ernst, R.R., Bodenhausen, G., Wokaun, A., (1990) Principles of Nuclear Magnetic Resonance, , Oxford Science Publications, Oxford, UK
Zolnai, Z., Juranic, N., Vikic-Topic, D., MacUra, S., (2000) J. Chem. Inf. Comput. Sci., 40, p. 611
Cobas, J.C., Martin-Pastor, M., (2004) EXSY Calc, Version 1.0, ©, , Mestrec, Universidad de Santiago de Compostela, Spain
Sandstrom, J., (1982) Dynamic NMR Spectroscopy, , Academic Press Inc. Ltd, London, pp. 80-81
Budzelaar, P.H.M., (1995) G-NMR, Version 4.0, , Cherwell Scientific Publishing, Palo Alto, CA, USA, ©
Angyal, S. J., (1980) Chem. Soc. Rev., 9, p. 41
Verchere, J. -F., Chapelle, S., Xin, F., Crans, D. C., (1998) Prog. Inorg. Chem., 47, p. 837
Brett, C. T., Waldron, K. W., (1990) The Physiology and Biochemistry of Plant Cell Wall, Ed., , Unwin Hyman, Chapman & Hall, London
Brown, W. H., Foote, C. S., (1998) Organic Chemistry, , Saunders College Publishing, Orlando, Florida, USA, 2nd edn
Angyal, S. J., (1991) Adv. Carbohydr. Chem. Biochem., 49, p. 20
Br nsted, J. N., Guggenheim, E. A., (1927) J. Am. Chem. Soc., 49, p. 2554
Ryu, K. -S., Kim, C., Kim, I., Yoo, S., Choi, B. -S., Park, C., (2004) J. Biol. Chem., 279 (24), p. 25544. , -25548
Sehray, K. J., Benkovic, S. J., (1978) Acc. Chem. Res., 2, p. 136. , -141
Sneyder, G. R., Serianni, A. S., (1991) Carbohydr. Res., 210, p. 21. , -38
Ramos, M. L., Caldeira, M. M., Gil, V. M. S., (1997) Carbohydr. Res., 297 (3), p. 191. , -200
Swain, C. G., (1950) J. Am. Chem. Soc., 72, p. 4578. , -4583
Swain, C. G., Brown, J. F., (1952) J. Am. Chem. Soc., 74, p. 2534. , -2538
O'Connor, C. J., Odell, A. L., Bailey, A. T., (1983) Aust. J. Chem., 36, p. 279. , -287
Beebe, J. A., Arabshahi, A., Clifton, J. G., Ringe, D., Petsko, G. A., Frey, P. A., (2003) Biochemistry, 42, p. 4414. , -4420
Isbell, H. S., Frush, H. L., Wade, C. W. R., Hunter, C. E., (1969) Carbohydr. Res., 9, p. 163. , -175
Serianni, A. S., Pierce, J., Huang, S. -G., Barker, R., (1982) J. Am. Chem. Soc., 15, p. 4037. , -4044
Ernst, R. R., Bodenhausen, G., Wokaun, A., (1990) Principles of Nuclear Magnetic Resonance, , Oxford Science Publications, Oxford, UK
Cobas, J. C., Martin-Pastor, M., (2004) EXSY Calc, Version 1. 0, , , Mestrec, Universidad de Santiago de Compostela, Spain
Budzelaar, P. H. M., (1995) G-NMR, Version 4. 0, , Cherwell Scientific Publishing, Palo Alto, CA, USA,
Tin(IV) catalyzed D-galacturonic acid anomerization
A comparative kinetic study of anomerization between the four main forms (α/β-pyranosides and α/β-furanosides) of d-galacturonic acid (GalAH2, 1) and tin(iv) complexed d-galacturonate ([Sn(CH 3)2(GalA)(H2O)2], 2) in D 2O, is reported. Important differences are shown by pD vs. mutarotation rate profiles of 1 and 2. Coordination, in fact, causes: i) a spectacular increase of the rate due to kinetic template assistance of the carboxylic tail holding the metal in close proximity to the reactive centre and ii) a change in the dependence of the rate on the pD. Entropic and enthalpic factors contribute to the huge activation energy decrease in 2. Anomerization rates of the complexed ligand are determined by 2D-EXSY cross-peak integration. Analysis of up to twelve direct and reverse rate constants in the pD range 7.0-2.5 evidences ring size memory, and at least one reaction path which bypasses the aldehydo open chain intermediate. Solvent oxygen atom incorporation into the ligand is, at pH 4.5, about ten fold faster when catalyzed by the metal, and proves that the metal-assisted nucleophilic attack of water on the anomeric carbon atom cannot significantly contribute to mutarotation rates that are thousands of times faster. © The Royal Society of Chemistry 2008.
A comparative kinetic study of anomerization between the four main forms (α/β-pyranosides and α/β-furanosides) of d-galacturonic acid (GalAH2, 1) and tin(iv) complexed d-galacturonate ([Sn(CH 3)2(GalA)(H2O)2], 2) in D 2O, is reported. Important differences are shown by pD vs. mutarotation rate profiles of 1 and 2. Coordination, in fact, causes: i) a spectacular increase of the rate due to kinetic template assistance of the carboxylic tail holding the metal in close proximity to the reactive centre and ii) a change in the dependence of the rate on the pD. Entropic and enthalpic factors contribute to the huge activation energy decrease in 2. Anomerization rates of the complexed ligand are determined by 2D-EXSY cross-peak integration. Analysis of up to twelve direct and reverse rate constants in the pD range 7.0-2.5 evidences ring size memory, and at least one reaction path which bypasses the aldehydo open chain intermediate. Solvent oxygen atom incorporation into the ligand is, at pH 4.5, about ten fold faster when catalyzed by the metal, and proves that the metal-assisted nucleophilic attack of water on the anomeric carbon atom cannot significantly contribute to mutarotation rates that are thousands of times faster. © The Royal Society of Chemistry 2008.
Tin(IV) catalyzed D-galacturonic acid anomerization
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Tin(IV) catalyzed D-galacturonic acid anomerization
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