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Tema 2

Aminocidos

Aminocidos
Sillares
estructurales de
las protenas

Estructuras
Propiedades cido-base
Curvas de titulacin
Punto isoelctrico

Aminocidos: Funciones

Estructura 3 D
de mioglobina

Estructura de aa

Structure: collagen (bone, cartilage,


tendon), keratin (hair), actin (muscle)
Enzymes: amylase, pepsin, catalase...
Transport: haemoglobin (oxygen),
transferrin (iron)
Hormones: insulin, glucagon
Antibodies:immunoglobulins

Amino acids are so-called because they have


both amino groups and acid groups, which
have opposite charges.
At neutral pH (found in most living organisms),
the groups are ionized
There is a positive charge at one end of the
molecule and a negative charge at the other
end.
The overall net charge on the molecule is
therefore zero.
A molecule like this, with both positive and
negative charges is called a zwitterion.

The charge on the amino acid


changes with pH
low pH (acid) neutral pH high pH (alkali)
charge = +1 charge = 0 charge = -1

For example: Gly

Ionizacin vs. pH

Punto isoelctrico
Valor de pH donde la carga media de un
aminocido es igual a cero
Clculo del pI: a travs de la ecuacin de
Henderson-Haselbalch
Polianfolitos: molcula con muchos grupos
ionizables (polipptidos)
Electroforesis: determinacin del pI
experimental

A pH fisiolgico predomina la forma zwiterinica

Isomera L y D
R representa la cadena lateral (residuo). Los
ismeros son imgenes especulares.

Ismero L
Es el nico presente en las protenas.
Corresponde a la configuracin S

La isomera es relativa a la molcula de


gliceraldehdo

Clasificacin segn grupo R

Alifticos: Gly, Ala, Val, Leu, Ile, Pro


Con OH: Ser, Thr
Con S: Cys, Met
Aromticos: Phe, Tyr, Trp
Bsicos: His, Lys, Arg
cidos: Asp, Glu (Asn, Gln)

Espectro de absorcin de aminocidos aromticos

Los 20
aminocidos

Ejercicio
Valores de
pKa para
algunos
aminocidos

What is the pI of histidine?


Datos:

For histidine
pKa1=2.3,
pKa2=6.0 and
pKa3=9.6.

Curvas de titulacin His

At the pI the net charge of the molecule is zero. To


find the pI, average the two pKa values on either
side of the neutral form of histidine.
(pKa2 + pKa3)/2 = pI
(6 + 9.6)/2 = 7.8
Draw out the titration curve for histidine to
convince yourself that the uncharged form is
predominant at this pH.

Aminocidos Esenciales

Arg
Met
His
Phe
Ile
Thr
Leu
Trp
Lys
Val
No son biosintetizados. Deben consumirse
en la dieta diaria

Aminocidos modificados
Fosfoserina
Hidroxiprolina

Algunos aa
no
proteicos
en la
naturaleza

Qu pasa si un aa reacciona con


otro aa?
Se forma un pptido
Cmo es el mecanismo qumico?

Reaccin Cys + Cys => Cistina

Enlace peptdico

Un tetrapptido
Formacin
del enlace
peptdico

Estructura del enlace peptdico

Hbrido de resonancia

Isomera cis - trans

Pptidos

Estructura primaria

When two amino acids join together a dipeptide


is formed.
Three amino acids form a tripeptide.
Many amino acids form a polypeptide:
+NH -Gly
3

Pro His Leu Tyr Ser Trp Asp Lys Cys-COO-

In a polypeptide there is always one end with a


free amino (NH3) group, called the N-terminus,
and one end with a free carboxyl (CO2) group,
called the C-terminus.