1. bookVolumen 14 (2021): Edición 1 (January 2021)
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eISSN
1339-3065
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10 Dec 2012
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Thermodynamic prediction of proton and hydrogen atom abstraction in dehydroascorbic acid and its bicyclic form

Publicado en línea: 30 Apr 2021
Volumen & Edición: Volumen 14 (2021) - Edición 1 (January 2021)
Páginas: 32 - 37
Detalles de la revista
License
Formato
Revista
eISSN
1339-3065
Primera edición
10 Dec 2012
Calendario de la edición
2 veces al año
Idiomas
Inglés
Abstract

Conformation analysis of dehydroascorbic acid and its bicyclic form was performed using the density functional theory. For the energetically preferred conformations, ionization potentials (IP) and bond dissociation enthalpies (BDE) were calculated using the B3LYP functional and 6-311++G** basis set. The effects of aqueous solution were estimated using the solvation model based on density (SMD) and the polarizable continuum model (IEF-PCM). The obtained results were compared with available experimental data for reference L-ascorbic acid (vitamin C). Our calculations indicate that the investigated bicyclic metabolic product of vitamin C can also exhibit limited radical scavenging ability due to the thermodynamically preferred dissociation of tertiary —CH bonds.

Keywords

Alongi KS, Shields GC (2010) Ann. Rep. Comp. Chem. 6: 113—138. Search in Google Scholar

Becke AD (1988) Phys. Rev. A 38: 3098—3100. Search in Google Scholar

Bendich A, Langseth L (1995) J. Am. Coll. Nutr. 14: 124—136. Search in Google Scholar

Bielski BHJ, Allen AO, Schwarz HA (1981) J. Am. Chem. Soc. 103: 3516—3518. Search in Google Scholar

Bielski BHJ, Cabelli DE, Arudi RL, Ross AB (1985) J. Phys. Chem. Ref. Data 14: 1041—1100. Search in Google Scholar

Binkley JS, Pople JA, Hehre WJ (1980) J. Am. Chem. Soc. 102: 939—947. Search in Google Scholar

Combs GF Jr., The Vitamins — Fundamental Aspects in Nutrition and Health, New York, Elsevier Academic Press, 2008, ISBN-13:978-0-12-183493-7. Search in Google Scholar

Deakin MR, Kovach PM, Stutts KJ, Wightman RM (1986) Anal. Chem. 58: 1474—1480. Search in Google Scholar

Fisher AJ, Ten Pas RH (1966) Anesth. Analg. 45 (5): 531—534. Search in Google Scholar

Flukiger P, Luthi HP, Portmann S, Weber J (2000—2002) MOLEKEL 4.3, Swiss Center for Scientific Computing, Manno Switzerland. Search in Google Scholar

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian 16, Revision B.01, Gaussian, Inc., Wallingford CT. Search in Google Scholar

Gutierrez PL (1988) Drug Met. Rev. 19: 319—343. Search in Google Scholar

Lengyel J, Rimarčík J, Vagánek A. Fedor J, Lukeš V, Klein E (2012) Food. Chem. 133: 1435—1440. Search in Google Scholar

Kurata T, Nishikawa Y (2000) Biosci. Biotechnol. Biochem. 64: 1651—1655. Search in Google Scholar

Lee C, Yang W, Parr RG (1988) Phys. Rev. B 37: 785—789. Search in Google Scholar

Merenich AV, Cramer CJ, Truhlar DG (2009) J. Phys. Chem. B 113: 6378—6396. Search in Google Scholar

Michalik M, Lukeš V (2016) Ac. Chim. Slov. 9: 89—94. Search in Google Scholar

Njus D, Kelley PM, Tu YJ, Schlegel HB (2020) F. Rad. Bio. Med. 159: 37—43. Search in Google Scholar

Pandithavidana DR, Jayawardana SB (2019) Molecules 24: 1646.10.3390/molecules24091646654013831027343 Search in Google Scholar

Rimarčík J, Lukeš V, Klein E, Ilcin M (2010) J. Mol. Struct. 952: 25—30. Search in Google Scholar

Shen K, Fu Y, Li JN, Liu L, Guo QX (2007) Tetrahedron 63: 1568—1576.10.1016/j.tet.2006.12.032 Search in Google Scholar

Škorňa P, Lengyel J, Rimarčík J, Klein E (2014) Comp. Theor. Chem. 1038: 26—32. Search in Google Scholar

Takahashi S, Cohen LA, Miller HK, Peake EG (1971) J. Org. Chem. 36: 1205—1209. Search in Google Scholar

Tomasi J, Mennucci B, Cammi R (2005) Chem. Rev. 105: 2999—3093. Search in Google Scholar

Tu YJ, Nius D, Schlegel HB (2017) Org. Biomol. Chem. 15: 4417—4431. Search in Google Scholar

Warren JJ, Tronic TA, Mayer JM (2010) Chem. Rev. 110: 6961—7001. Search in Google Scholar

Wilson JX (2002) FEBS Lett. 527: 5—9. Search in Google Scholar

Wyman GM (1955) Chem. Rev. 55: 625—657. Search in Google Scholar

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