Disciplina: SQM0485 - nequimed.iqsc.usp.brnequimed.iqsc.usp.br/files/2017/02/Aula3.pdf · Amidas 17...
Transcript of Disciplina: SQM0485 - nequimed.iqsc.usp.brnequimed.iqsc.usp.br/files/2017/02/Aula3.pdf · Amidas 17...
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Disciplina: SQM0485
Prof. Dr. Andrei Leitão
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Ácidos carboxílicos e derivados, Sulfidrilas, Fosfatos Orgânicos e
grupos Aromáticos e Heteroaromáticos
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Ácidos carboxílicos e derivados
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Propriedades & reatividade
4
Reatividade Derivado
Grupo
abandonador Basicidade
Mais reativo
Menos reativo
Cloreto
Ácido
Anidrido
Éster
Amida
Carboxilato
Menor
Maior
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Interconversão de derivados
5
anidrido
cloreto de
acila
éster
amida
carboxilato
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Nomenclatura dos derivados
6
Cloreto de pentanoíla Anidrido pentanoico
Pentanonitrila
Pentanoato de metila Pentanamida
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Haletos de acila (haletos de ácido)
7
cloreto de o-metoxibenzoila (E)cloreto de 2-octenoila
cloreto de (p-metoxifenil)acetila
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Anidridos
8
Anidrido butanoico Anidrido acético benzoico
Ácido succínico Anidrido succínico
Diidrofuran-2,5-diona Ácido butanodioico
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Ésteres
9
Benzoato de propila (Z)2-butenoato de ciclopentila
Ciclohexanocarboxilato de isobutila Fenilacetato de etila
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Ésteres (2)
10
acetato de isopentila
usado como sabor
artificial de banana
pentanoato de isopentila
usado como sabor
artificial de maçã
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Lipids
11
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Ácidos graxos
12
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Ácidos graxos (1)
13
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Ácidos graxos
14
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Glycerol and triacylglycerol
15
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Ceras
16
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Amidas
17
m-methylbenzamida 2-etil-3-metilpentanamida α-etil-β-metilvaleramida
N,N-dimetilciclopentanocarboxamida N-benzilformamida
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Lactonas
18
ácido δ-hidroxivalérico δ-valerolatona
Ácido γ-hidroxienâtico γ-enantolactona
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Ácidos dicarboxílicos
19
ácido etanodioico ácido butanodioico ácido hexanodioico
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Nitrilas
20
Pentanonitrila Propenonitrila Benzonitrila
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Estruturas químicas
21
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Ácidos carboxílicos
Teste de solubilidade em água
22
ácido benzoico
(insolúvel em água)
benzoato de sódio
(solúvel em água)
Pode ser feito para diferenciar ácidos de fenóis insolúveis
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Teste de solubilidade em água (2)
23
fenol
(insolúvel em água)
fenolato sódio
(solúvel em água)
Pode ser feito para diferenciar ácidos de fenóis insolúveis
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Influência dos substituintes no pKa
24
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Amino acids
25
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Stereoisomery
26
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Nonpolar & aromatic amino acids
27
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Properties
28
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Polar & charged amino acids
29
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Properties
30
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Zwitterions
31
Amphoters
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Titration curve
32
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Titration curves
33
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Effect of the chemical environment
34
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Peptides
35
Condensation reaction
Pentapeptide
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Peptides
36
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Proteins
37
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3D structure of proteins
38
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3D structure of proteins
39
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3D structure
of proteins
40
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Sulfidrila e fosfato orgânico
41
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Sulfidrila
42
Presente em cisteína como grupo reativo em cisteíno proteases
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Fosfolipídeos e membrana celular
43
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Fosfolipídeos e membrana celular (2)
44
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Fats everywhere...
45
Fat stores inside the cell
Get a detergent and check its
chemical composition...
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Estruturação do DNA e RNA
46
Bases
nitrogenadas
Açúcar
Fosfato
K+
H2O
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Nucleoside phosphates
47
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Nucleoside phosphates
48
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Compostos aromáticos e heteroaromáticos
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Aromático vs. insaturado
50
Estabilidade maior dos compostos aromáticos
Planaridade do anel e conjugação das insaturações
A aromaticidade e a regra de Hückel
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Compostos aromáticos
51
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Compostos aromáticos
52
Benzeno
Piridina Pirrol
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Reatividade & aromaticidade
53
Ciclopropeno cátion ânion
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Reatividade & aromaticidade
54
Ciclopentadieno
etano
Base conjugada
Base conjugada
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Reatividade & aromaticidade
55
7-bromociclohepta-1,3,5-trieno íon tropílio
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Compostos aromáticos policíclicos
e heteroaromáticos
56
naftaleno fenantreno criseno
piridina pirrol furano tiofeno
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Compostos aromáticos policíclicos
e heteroaromáticos
57
piridina
Orbital p que interage no
sistema aromático
Orbital sp2 fora do sistema
aromático
pirrol furano
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Outros compostos heteroaromáticos
58
quinolina indol imidazol purina pirimidina
Bases nitrogenadas
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Compostos antiaromáticos
59
Compostos antiaromáticos são menos estáveis dos que os
não aromáticos e os aromáticos
São planos, com duplas ligações alternadas e número de
elétrons π = 4n
Ciclobutadieno e o cátion ciclopentadienila são muito instáveis
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Aromático vs. antiaromático
60
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Nomenclatura
61
Aromáticos monossubstituídos
bromobenzeno clorobenzeno nitrobenzeno etilbenzeno
tolueno fenol anilina ácido benzenossulfônico
metilbenzeno
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Nomenclatura
62
metoxibenzeno fenileteno benzaldeído ácido benzoico benzonitrila
anisol estireno aldeido benzoico
isopropilbenzeno 2-fenilbutano 2-metil-2-fenilpropano
cumeno sec-butilbenzeno tert-butilbenzeno
Aromáticos monossubstituídos
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Nomenclatura (2)
63
grupo fenila grupo benzila
clorometilbenzeno éter fenílico éter benzílico
cloreto de benzila
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Reatividade
64
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Redução do benzeno
65
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Acidez do fenol e do ácido benzoico
66
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Exemplos de heteroaromáticos
67
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Exemplos de grupos funcionais
68 Hadjuk, P.J.; Greer, J. Nature Rev. Drug Discov. 2007, 6, 211
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Exemplos de grupos funcionais (2)
69 Hadjuk, P.J.; Greer, J. Nature Rev. Drug Discov. 2007, 6, 211
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Propriedade físico-química
70
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Deoxyribonucleotides
71
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Ribonucleotides
72
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DNA
73