FUNDACIÓN UNIVERSIDAD DE AMÉRICA

TALLER DE CARBOHIDRATOS, LÍPIDOS Y AMINOÁCIDOS

Asignatura: Bioquímica.
Fecha: Septiembre de 2020.
Docente: David Leonardo Sotelo.
Valor en el segundo corte: 10 %

Nombre:_____________________________________ Código:_______________

Nombre:_____________________________________ Código:_______________

Nombre:_____________________________________ Código:_______________

I. Sección de carbohidratos y polisacáridos.

1. Los carbohidratos son considerados moléculas ópticamente activas ¿Cuál es la razón?

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2. Describa las diferencias estructurales comunes y las diferencias para cada par de
azucares:

a. D-glucosa y D-fructosa:
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b. Maltosa y sacarosa:
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c. Glucógeno y amilopectina:
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3. ¿Qué significa que un carbono sea un anómero?

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C-1 of the first-named sugar residue is joined to
otometrically. (hemolymph) of insects, serving as an energy-storage
the second. (4) Name the second residue. If there compound.
hird
_238-272residue,11/21/03
describe the 7:38 secondAM glycosidic
Page 243 bond Mac113 mac113:122_EDL:
ecing
same disaccharides
conventions. such(To as maltose
shortenun- the description 6 CH OH
2
6 CH OH
2
especially
mplex polysaccharides,to name
4. Dos carbohidratosmore complex
three-letterque abbreviations
se unen por el enlace glicosídico O originalmente uno de ellos
O
5 5
several rules arees followed.
considerable
e monosaccharides are often used, as given inBy conven- como un hemiacetal o HO
hemicetal H y el otro como Hun alcohol.
H OH
Esta
scribes the
7–1.) Following compound
afirmación with its
es:
this convention nonre- a.for
Verdadera.
naming 4
b. Falsa. OH Sustente 1 " O 4
su respuesta: 1 "
H OH H
left, and we can “build up” the name
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accharides, maltose is !-D-glucopyranosyl-(1n4)- H H H
rder. (1) Give the configuration (! or
opyranose.__________________________________________________________________________
3 2 3 2
Because most sugars encountered in H OH Chapter 7 Carbohydrates H OH
ric carbon joining the first monosac- and Glycobiol
ook are the D enantiomers and the pyranose form Lactose ( " form)
the left) to 5. the Escriba
second. debajo(2) Name the
de usecadaa estructura
oses predominates, we generally shortened si se trata de su forma alfa o beta, y explique en las
" -D-galactopyranosyl-(1n4)-" -D-glucopyranose
líneas posteriores como puede se referencian estas isomeríasGal( (alfa y beta):
" 1n4)Glc
n of the formal name of such compounds, giving
onfiguration of6 CH the2OH anomeric carbon and naming the hydroxyl group at C-6 of L-galactose o
6 CH OH
5 CH OH
arbons joined by the Oglycosidic bond. 6In this ab-
2
2
produces L-fucose 1
or L-rhamnose, respect
O O 1 O HOCH
ted hemiacetalH H HOCH CH OH 5 2
O inHplant polysaccha
H nomenclature, HH maltose is OH Glc(!1n4)Glc. H H deoxy sugars H are found
2 2
4 H 1
he disaccharide! OHlactose H (Fig. 7–12), which 5
H yields
HO 2 4 theHcomplex1 ! oligosaccharide
" 2
H HO
5 components
OH H OH
ctose
OH and HO D-glucose
HO OH H
on hydrolysis, occurs
H natu- OH HO teins and glycolipids. CH OH
3 2 O 6
2
4 3
only in milk. The anomeric carbon of the glucose 3 2
Oxidation of the
3 4
alcohol OHcarbonyl
H (aldehyde) ca
e is available Hfor oxidation, OH OH
H
and thus OH H
lactose H OH
cose to the carboxyl level produces gluconic
_______ $ -D-Glucose
! -D-Glucopyranose ! -D_______
-Fructofuranose _______ Sucrose ________
educing disaccharide. Its abbreviated name is
hydrolysis condensation
! - aldoses yield other aldonic acids. Oxidatio
D-glucopyranosyl " -D -fructofuranoside
1n4)Glc. Sucrose (table sugar) is a disaccharide Glc(! 1 nn2")Fru
H O
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H OCH OH bon at the other end of the carbon chain—C-
cose and fructose.
2 2 2It is formed by plants but not
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mals. In contrast O
to maltose and lactose, sucrose OH
6 CHgalactose,
2OH
or mannose—forms H the correspon
OH H 6 CH
2OH OH HOCH2 O
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ns H 5 O glucuronic, galacturonic, O 5 or mannuron
O no free acetalanomeric carbon O atom; the anomeric
hemiaceta 5
H Haldonic H OH
ns ofHboth monosaccharide
H OH H H units are involved
OH H HOin and uronic acids6 form HOCH 2 stable intram
HO 4 1H H CH OH 4 1 ! O ! 1 4
H
1
ycosidic bondII. (Fig. OH 7–12).
Sección H Sucrose
de Lípidos. is therefore a 2 OHters called lactones (Fig. 7–9, lower left). In
H OH H
H HO H H
ducing sugar.
O HNonreducing
OH disaccharides OH are
H these
3 2
acidic hexose derivatives,
2 3
one nine-c
2 3 2
dOH as glycosides; in
H this case, the positions joined tienen puntos de Hsugar deserves mention: N-acetylneuraminic
"1. ¿Por qué
-D-Glucopyranose OH los ácidos grasos saturados
" -D-Fructofuranose fusiónOH y ebullición másH altos OHde los
e anomeric Maltose insaturados?
carbons. In the abbreviated nomen- acid, but often
Trehalose referred to simply as “sialic
e, __________________________________________________________________________
a double-headed arrow connects the symbols ! -D-glucopyranosyl ! -D-glucopyranoside
pyranosyl-(1n4)- D-glucopyranose
O rivativeGlc( of!N-acetylmannosamine,
1n
n1!)Glc is a compon
HC O
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ying the anomeric carbons and their configura-
ion of maltose. A disaccharide is formed from HC glycoproteins and glycolipids in animals. Th
For example, the abbreviated name of sucrose CH
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(here, two HC molecules of D-glucose) CH when an FIGURE 7–12 Some acidcommon
groupsdisaccharides.
of the acidic Like sugar
maltosederivatives
in Figure a
er Glc(!1m n 2")Fru or Fru("2m
e glucose molecule (right) condenses with the n 1!)Glc. Sucrose
C metabólica
C 7–11, these are shown as Haworth perspectives. The
pH 7, and the compounds are therefore corr common name,
ajorofintermediate2. Explique product cual of esphotosynthesis;
la importancia in del ácido linoleico:
cetal the otherHglucose
2C CH
molecule (left), with H H full systematic name, and abbreviation are given for each disaccharide.
as the carboxylates—glucuronate, galacturo
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nd formation of an O-glycosidic bond. The re-
Pyran Furan
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is hydrolysis—attack by H2O on the glycosidic
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olecule
FIGUREretains7–7 TABLE
a reducing
Pyranoses 7–1
hemiacetal Abbreviations
at the
and furanoses. for Common
The pyranose formsMonosaccharides
of D-
e glycosidic
glucose 3. bond.
andDibujeand
Because Some
the furanose of
mutarotation Their Derivatives
inter-
forms ofdeD-fructose
la estructura un ácidoare grasoshown here as16:1
omega-6
orms of the hemiacetal, the bonds at this posi-
Haworth perspective formulas. The edges of the ring nearest the reader
picted with wavy lines, Abequose
as shown here, to indi- Abe Glucuronic acid GlcA
Axis Axi
are represented by bold lines. Hydroxyl groups below the plane of the
may be either ! or ". Arabinose Ara Galactosamine GalN
ring in these Haworth ax ax
Fructoseperspectives Fru would appear at the right side of
Glucosamine GlcN
a Fischer projection eq O
Fucose(compare withFuc Fig. 7–6). Pyran N-Acetylgalactosamine
and furan are eq GalNAcax eq
ax
shown for comparison. Galactose Gal N-Acetylglucosamine GlcNAc
4. Realice una descripción y dibuje un ejemplo de cada uno eq ax siguientes lípidos
de los eq eqde
Glucose
membrana: Glc Iduronic acid IdoA eq eq
Mannose Man Muramic acid axMur ax ax
whereas a.two Rhamnose Rha
configurations can be interconverted only
Glicerofosfolípidos: N-Acetylmuramic acid Mur2Ac
Two possible chair forms
Ribose
by breaking a covalent bond—for Rib example, N-Acetylneuraminic
in the case acid Neu5Ac
(a)
Xylose Xyl (a sialic acid)
of ! and " configurations, the bond involving the ring
oxygen atom. The specific three-dimensional confor- Axis
mations of the monosaccharide units are important in H
determining the biological properties and functions of H2COH O
HO H
some polysaccharides, as we shall see.
H H
HO
 3.1 Amino Acids 81

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FIGURE 3–8 Uncommon amino acids. (a) Some uncommon amino
H
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acids found in proteins. All are derived from common amino acids.
HO C CH2
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Extra functional groups added by modification reactions are shown in
H2C !
CH COO" red. Desmosine is formed from four Lys residues (the four carbon back-
N bones are shaded in yellow). Note the use of either numbers or Greek
H H b. Galactolípidos: letters to identify the carbon atoms in these structures. (b) Ornithine
4-Hydroxyproline and citrulline, which are not found in proteins, are intermediates in
the biosynthesis of arginine and in the urea cycle.
2 CH CH2 CH2 CH COO"
OH !
NH3
5-Hydroxylysine
O O
HO C O
"
C
H2 CH2 CH2 CH2 CH COO" !
H2N C H H 3N C H
!
NH3
R R
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6-N-Methyllysine
Nonionic Zwitterionic
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form form
COO" __________________________________________________________________________
FIGURE 3–9 Nonionic and zwitterionic forms of amino acids. The
OOC CH CH2 CH COO" nonionic form does not occur in significant amounts in aqueous so-
c.! NH
Esfingolípidos:
3 lutions. The zwitterion predominates at neutral pH.
# -Carboxyglutamate

!
H3N COO"
CH
Amino Acids Can Act as Acids and Bases
(CH2)3 ! When an amino acid is dissolved in water, it exists in so-
NH 3
lution as the dipolar ion, or zwitterion (German for
CH2)2 (CH2)2 CH “hybrid ion”), shown in Figure 3–9. A zwitterion can act
!
COO" as either an acid (proton donor):
N
(CH2)__________________________________________________________________________
4 H H
CH __________________________________________________________________________
R C COO" R C COO" ! H!
!
H3N __________________________________________________________________________
COO"
!
NH3 NH2
Desmosine
Zwitterion
5. Presente un ejemplo de una hormona esteroidéa y describa su importancia metabólica:
HSe CH2 CH COO"
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or a base (proton acceptor):
!
NH__________________________________________________________________________
3
Selenocysteine
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H H
R C COO" ! H! R C COOH
!
NH3 !
NH3
! III. Sección de aminoácidos.
Zwitterion
3N CH2 CH2 CH2 CH COO"
!
NH3
1. Identifique
Ornithine cual de Substances having moléculas
las siguientes estáareenamphoteric
this dual nature su forma Zwitterion y describa la
and are often called ampholytes (from “amphoteric
definición de ese termino, su relación con el pH y el punto isoeléctrico del aminoácido:
electrolytes”). A simple monoamino monocarboxylic !-
C N CH2 __________________________________________________________________________
CH2 CH2 CH COO" amino acid, such as alanine, is a diprotic acid when fully
O H __________________________________________________________________________
!
NH3 protonated—it has two groups, the OCOOH group and
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Citrulline the ONH! 3 group, that can yield protons:

H H! H H! H
R C COOH R C COO " R C COO"
ve special note because they are key
etabolites) in the biosynthesis of argi- Net
!
NH3 !
NH3 NH2
and in the urea cycle (Chapter 18). charge: !1 0 "1
2. Dibuje la estructura, indique el código de tres letras, de una letra y clasifique de acuerdo a
su cadena radical, cada uno de los 20 aminoácidos esenciales:

Fenilalanina Glicina Aspartato

Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________

Glutamato Metionina Tirosina

Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________

Prolina Triptofano Alanina

Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________
 Serina Valina Lisina
Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________

Treonina Histidina Leucina

Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________

Isoleucina Asparagina Glutamina

Código tres letras: __________ Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________ Clasificación R: _____________
 Cisteina Arginina
Código tres letras: __________ Código tres letras: __________
Código una letra: ___________ Código una letra: ___________
Clasificación R: _____________ Clasificación R: _____________

3. En un aminoácido cualquiera, indique a que corresponde el valor de pK1 y pK2.

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4. ¿Por qué algunos aminoácidos tienen valores de pKR?

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5. Explique porqué se dice que el enlace peptídico es un enlace sencillo con cara de
doble. De ser posible, dibuje una estructura química que le permita demostrarlo:
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