Calçad

Química - Frente 1

Proteínas
a

Estrutura
 Secundária
Quaternária

Terciária

Primária
 COOH
Table 26-1 Natural (2S)-Amino Acids H2N H
R

Three-letter One-letter pKa of pKa of pKa of acidic Isoelectric

R Name code code A-COOH A-!NH3 function in R point, pI
H Glycine Gly G 2.3 9.6 — 6.0
Alkyl group
CH3 Alanine Ala A 2.3 9.7 — 6.0
CH(CH3)2 Valinea Val V 2.3 9.6 — 6.0
CH2CH(CH3)2 Leucinea Leu L 2.4 9.6 — 6.0
CHCH2CH3 (S) Isoleucinea Ile I 2.4 9.6 — 6.0
A
CH3

H2C Phenylalaninea Phe F 1.8 9.1 — 5.5

COOHb
HN H Proline Pro P 2.0 10.6 — 6.3
CH2

Hydroxy containing
CH2OH Serine Ser S 2.2 9.2 — 5.7
CHOH (R) Threoninea Thr T 2.1 9.1 — 5.6
A
CH3

H2C OH Tyrosine Tyr Y 2.2 9.1 10.1 5.7

Amino containing
O
B
CH2CNH2 Asparagine Asn N 2.0 8.8 — 5.4
Continued
Table 26-1 Natural (2S)-Amino Acids (continued)
Three-letter One-letter pKa of pKa of pKa of acidic Isoelectric
R Name code code A-COOH A-!NH3 function in R point, pI
Amino containing (continued)
O
B
CH2CH2CNH2 Glutamine Gln Q 2.2 9.1 — 5.7
(CH2)4NH2 Lysinea Lys K 2.2 9.0 10.5c 9.7
NH
B
(CH2)3NHCNH2 Argininea Arg R 2.2 9.0 12.5c 10.8
H2C

Tryptophana Trp W 2.8 9.4 — 5.9

N
H
H2C
NH Histidinea His H 1.8 9.2 6.1c 7.6

N
Mercapto or sulfide containing
CH2SH Cysteined Cys C 2.0 10.3 8.2 5.1
CH2CH2SCH3 Methioninea Met M 2.3 9.2 — 5.7
Carboxy containing
CH2COOH Aspartic acid Asp D 1.9 9.6 3.7 2.8
CH2CH2COOH Glutamic acid Glu E 2.2 9.7 4.3 3.2
a
Essential amino acids. bEntire structure. cpKa of conjugate acid. dThe stereocenter is R because the
CH2SH substituent has higher priority than the COOH group.
 R

=
O
H23N C C
+
O-H
H
Estrutura secundária - a alfa-hélice
Folha pregueada, ou folha beta
Desnaturação
 a) interações iônica

b) Ligações de hidrogêni

c) Pontes de dissulfet

d) Interações hidrofóbicas
S
|

Lipídios
Ácidos graxos: ác. carboxílicos de cadeia longa
SATURADO INSATURADO

Cadeia lateral
CnH2n+1

CnH2n-1

CnH2n+1

CnH2n+1
 Stearic acid

Figure 5.12
(a) Saturated fat and fatty acid
 Oleic acid

cis double bond

ure 5.12 (b) Unsaturated fat and fatty acid causes bending
 CH2 +
Choline
Hydrophilic head
N(CH3)3
CH2
O
O P O–
Phosphate
O
CH2 CH CH2
Glycerol
O O
C O C O

Fatty acids
Hydrophobic tails

Hydrophilic
head
Hydrophobic
tails

(c) Phospholipid
(a) Structural formula (b) Space-filling model symbol
CARBOIDRATOS
 Model Bu
Model Building
How to Draw l-Amino Acids and Their Relation to the l-Sugars
hashed-wedged line structures or by Fischer
d line Nstructures
O
H N or by Fischer
A
COOH
´
2
O C2, or !-carbon
O COOH CHO
C O COOH H2N # C ! H H2N H HO H
≥ N

#
≥
R R R CH2OH
O H R
S (L) R (S)-2,3-Dihydroxypropanal
(L-Glyceraldehyde)

l-Amino Acids Hashed-wedged

and Their Relation to the l-Sugars
line structures Fischer projections

s and Their Relation to the l-Sugars

In all but glycine, the simplest of the amino acids, C2 is a stereocenter and usually adopts
arbon
the S configuration. Other stereocenters located in the substituent R may have either R (as
COOH O
in threonine) or S configuration (as in isoleucine).
O´ O COOH
As in the names of the sugars (Section 24-1), an older amino acid nomenclature uses
CHO
OH COOH
the prefixes d and l, which relate all the l-amino acids to (S)-2,3-dihydroxypropanal (l-
O CHO
H N# C !H HN
glyceraldehyde). As emphasized in the discussion of the natural d sugars, a molecule belong-
2 5 113.9)
ing to the2l family is not necessarily levorotatory. For example, both valine ([a]258C
H HO H
!H ≥ 258C HN N
and isoleucine ([a]d 5 111.9) are dextrorotatory. 2 H d
HO H
NR R CH2OH
RR 2OH
CH(S)-2,3-Dihydroxypr
R (L-Glyceraldehy
(S)-2,3-Dihydroxypropanal
ine structures (L-Glyceraldehyde)
Fischer projections
Fischer projections

acids, C2 is a stereocenter and usually adopts

ted in the substituent
stereocenter R may
and usually have either R (as
adopts
 Five- and Six-Membered Cyclic Hemiacetal Formation
New
stereocenter

OH HA H
O A O

A
H!
A

A
H2C 4 C O H2C 4 1C

A
A A1 A A OH
H2C CH2 H2C CH2
A

A
3 2 3 2
Furanose ring Furan

New
stereocenter
O OH
H2C 5 H H2C5 OA O

A
H
O
O

! A
H
H2C 4 C O H2C 4 1C
O
B

1 A A
O

H2C CH2 H2C CH2 OH

A

A
3 2 3 2
Pyranose ring Pyran

o depict a d-series sugar correctly in its cyclic form, draw the hashed-wedged line
entation of the all-eclipsed structure on the previous page and flip it upside down, as
fi
m