Draw the peptide ASK(ala-ser-lysine) with proper stereochemistry? what is its pI(isoelectric point)and why the structure is planar? Use the following table to look at pka's of the amino acids and solve this question. TABLE 5.1 Properties of the common amino acids found in proteinspk, of c-COOHGroupNameAlanineArginineAsparagineAspartic acidCysteineGlutamineGlutamic acidGlycineHistidineIsoleucineLeucineLysineMethioninePhenylalanineProlineSerineThreonineTryptophanTyrosineValineAbbreviations: 1-and 3-letter codesA, AlaR, ArgN, AsnD, AspC, CysQ, GlnE, GluG, GlyH, His1, lleL, LeuK, LysM, MetF, PheP, ProS, SerT, ThrW. TrpY, TyrV, Val2.32.22.02.11.82.22.22.31.82.42.42.22.31.82.02.22.62.42.22.3pk, of a-NH₂Group9.79.08.89.810.89.19.79.69.29.79.69.09.29.110.69.210.49.49.19.6pk, of lonizingSide Chain12.53.98.34.2-6.0-10.010.1Residue Mass(daltons)71.08156.20114.11115.09103.14128.14129.1257.06137.15113.17113.17128.18131.21147.1897.1287.08101.11186.21163.1899.14Occurrence inProteins (mol %)8.75.04.25.91.33.76.67.92.45.58.95.52.04.04.75.85.61.53.57.2

Answered: Draw the peptide ASK(ala-ser-lysine)…

Biochemistry

9th Edition

ISBN:9781319114671

Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Chapter1: Biochemistry: An Evolving Science

Section: Chapter Questions

Problem 1P

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Question

Draw the peptide ASK(ala-ser-lysine) with proper stereochemistry? what is its pI(isoelectric point)and why the structure is planar? Use the following table to look at pka's of the amino acids and solve this question.

TABLE 5.1 Properties of the common amino acids found in proteins
pk, of c-COOH
Group
Name
Alanine
Arginine
Asparagine
Aspartic acid
Cysteine
Glutamine
Glutamic acid
Glycine
Histidine
Isoleucine
Leucine
Lysine
Methionine
Phenylalanine
Proline
Serine
Threonine
Tryptophan
Tyrosine
Valine
Abbreviations: 1-
and 3-letter codes
A, Ala
R, Arg
N, Asn
D, Asp
C, Cys
Q, Gln
E, Glu
G, Gly
H, His
1, lle
L, Leu
K, Lys
M, Met
F, Phe
P, Pro
S, Ser
T, Thr
W. Trp
Y, Tyr
V, Val
2.3
2.2
2.0
2.1
1.8
2.2
2.2
2.3
1.8
2.4
2.4
2.2
2.3
1.8
2.0
2.2
2.6
2.4
2.2
2.3
pk, of a-NH₂
Group
9.7
9.0
8.8
9.8
10.8
9.1
9.7
9.6
9.2
9.7
9.6
9.0
9.2
9.1
10.6
9.2
10.4
9.4
9.1
9.6
pk, of lonizing
Side Chain
12.5
3.9
8.3
4.2
-
6.0
-
10.0
10.1
Residue Mass
(daltons)
71.08
156.20
114.11
115.09
103.14
128.14
129.12
57.06
137.15
113.17
113.17
128.18
131.21
147.18
97.12
87.08
101.11
186.21
163.18
99.14
Occurrence in
Proteins (mol %)
8.7
5.0
4.2
5.9
1.3
3.7
6.6
7.9
2.4
5.5
8.9
5.5
2.0
4.0
4.7
5.8
5.6
1.5
3.5
7.2

Expert Solution

Step 1: Peptide

Given peptide is ASK( alanine- serine- lysine).

The peptide is planar due to the partial double bond character of peptide bond. A peptide bond is formed between alpha- carboxy group of one amino acid and alpha- amino group of another amino acid. The peptide bond is a stable covalent bond and is planar because it has partial double bond character, due to the delocalization of electrons from the double bonded oxygen to the peptide bond.