Química Biorgânica – 2009 Programa
Horário: 4 feiras: 14:30-17:30 hs.
Local: Instituto de Química, Sala 03 Bl. 06 Inferior
aula
1
Data
Tópicos
07/10
Apresentação do curso. Aspectos gerais da química de produtos naturais.
Evolução biológica. Biossíntese de lipídeos.
2
14/10
Seminários de alunos.
4
21/10
Policetídeos aromáticos. Reações de condensação. Uso de marcação
isotópica em estudos de biossíntese. Discussão de problemas.
5
23/10
Seminários de alunos (continuação).
(9:00 h)
5
28/10
Via do ácido chiquímico. Compostos fenólicos em geral. Flavonóides.
Fenilpropanóides,
lignanas,
neolignanas
e
análogos.
Reações
de
acoplamento oxidativo. Discussão de problemas.
6
04/11
Biossíntese de terpenóides: mono- e sesquiterpenos. Biossíntese de
terpenóides:
triterpenos,
tetraterpenos
e
esteróides.
Discussão
de
problemas.
7
06/11
Discussão de problemas.
(9:00 h)
8
18/11
Alcalóides derivados da ornitina e lisina. Reações de Mannich. Alcalóides
derivados de aminoácidos aromáticos. Discussão de problemas.
9
25/11
Não haverá aulas.
10
02/12
Seminários de alunos.
e-mail: majokato@iq.usp.br; 3818-3813
Referências
Croteau, R., Kutchan T. M. and Lewis N. G. (2000) Natural Products (Secondary
Metabolites). In Biochemistry & Molecular Biology of Plants, B. Buchanan, W.
Gruissem, R. Jones, Eds., American Society of Plant Physiologists.
Dewick, P. M. (2002) Medicinal Natural Products - A Biosynthetic Approach. Second Edition
John Wiley & Sons Ltd. England.
Geissman, T.A. & Crout, D.H.G (1969) Organic Chemistry of Secondary Plant Metabolism.
Freeman, Cooper & Company. California. 591 p.
Luckner, M. (1990) Secondary Metabolism in Microorganism, Plants and Animals. VEB
Gustav Fisher Verlag Jena.
Mann J. (1994) Chemical Aspects of Biosynthesis. Oxford Science Publications, p. 92.
Aula 1 (evolução biológica):
Orgel, L. E., 1998. The origin of life - a review of facts and speculations. Trends Biochem. Sci.
23, 491-495.
Segre, D., Lancet, D., 2000. Composing life. EMBO Rep. 1, 217-222.
Torchet, C., Maurel, M.-C., 2007. RNAs in Extreme Environments. Chem. Biodiversity 4,
1957-1971.
Anet, F. A., 2004. The place of metabolism in the origin of life. Curr. Opin. Chem. Biol. 8, 654659.
Trevors, J. T., 2003. Early assembly of cellular life. Prog. Biophys. Mol. Biol. 81, 201-217.
Deamer, D., Dworkin, J. P., Sandford, S. A., Bernstein, M. P., Allamandola, L. J., 2002. The
first cell membranes. Astrobiology 2, 371-381.
Koonin, E. V., 2007. The Biological Big Bang model for the major transitions in evolution. Biol.
Direct 2:21.
Deamer, D., 2009. On the origin of systems - Systems biology, synthetic biology and the
origin of life. EMBO Rep. 10, S1-S4.
Firn, R. D., Jones, C. G., 2009. A Darwinian view of metabolism: molecular properties
determine fitness. J. Exp. Bot. 60, 719-726.
Hartmann, T., 2007. From waste products to ecochemicals: Fifty years research of plant
secondary metabolism. Phytochemistry 68, 2831-2846.
Aula 4 (policetídeos):
Bentley, R., Bennett, J. W., 1999. Constructing polyketides: From Collie to combinatorial
biosynthesis. Annu. Rev. Microbiol. 53, 411-446.
Hertweck, C., 2009. The Biosynthetic Logic of Polyketide Diversity. Angewandte ChemieInternational Edition 48, 4688-4716.
Yu, O., Jez, J. M., 2008. Nature's assembly line: biosynthesis of simple phenylpropanoids and
polyketides. Plant J. 54, 750-762.
Staunton, J., Weissman, K. J., 2001. Polyketide biosynthesis: a millennium review. Nat. Prod.
Rep. 18, 380-416.
Aula 5 (via do ácido chiquímico):
Ferrer, J. L., Austin, M. B., Stewart, C., Noe, J. P., 2008. Structure and function of enzymes
involved in the biosynthesis of phenylpropanoids. Plant Physiology and Biochemistry 46,
356-370.
Boudet, A.-M., Evolution and current status of research in phenolic compounds.
Phytochemistry 68, 2722-2735.
Wilson, D. J., Patton, S., Florova, G., Hale, V., Reynolds, K. A., 1998. The shikimic acid
pathway and polyketide biosynthesis. J. Ind. Microbiol. Biotechnol. 20, 299-303.
Aula 6 (terpenoides):
Eisenreich, W., Rohdich, F., Bacher, A., 2001. Deoxyxylulose phosphate pathway to
terpenoids. Trends Plant Sci. 6, 78-84.
Kuzuyama, T., 2002. Mevalonate and nonmevalonate pathways for the biosynthesis of
isoprene units. Biosci. Biotechnol. Biochem. 66, 1619-1627.
Eisenreich, W., Bacher, A., Arigoni, D., Rohdich, F., 2004. Biosynthesis of isoprenoids via the
non-mevalonate pathway. Cell. Mol. Life Sci. 61, 1401-1426.
Withers, S. T., Keasling, J. D., 2007. Biosynthesis and engineering of isoprenoid small
molecules. Appl. Microbiol. Biotechnol. 73, 980-990.
Aula 8 (alcaloides):
Kutchan, T. M., 1995. Alkaloid biosynthesis - The basis for metabolic engineering of medicinal
plants. Plant Cell 7, 1059-1070.
Facchini, P. J., 2001. Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular
regulation, and metabolic engineering applications. Annu. Rev. Plant Physiol. Plant Mol.
Biol. 52, 29-66.
Facchini, P., Bird, D., Bourgault, R., Hagel, J. M., Liscombe, D., MacLeod, B. P., Zulak, K. G.,
2005. Opium poppy: a model system to investigate alkaloid biosynthesis in plants.
Canadian Journal of Botany-Revue Canadienne De Botanique 83, 1189-1206.
Zenk, M. H., Juenger, M., 2007. Evolution and current status of the phytochemistry of
nitrogenous compounds. Phytochemistry 68, 2757-2772.
Referências complementares:
Bentley, R., 1999. Secondary metabolite biosynthesis: The first century. Crit. Rev. Biotechnol.
19, 1-40.
Scott, A. I., 1996. Travels of an organic chemist along nature's pathways. Bioorg. Med. Chem.
4, 965-985.
Battersby, A. R., 1996. The marvels of biosynthesis: Tracking nature's pathways. Bioorg.
Med. Chem. 4, 937-964.