del 2: Structures and abbreviations of the 20 standard amino acids in form, Hydrophobic amino acids COO witterionic classified according to their side chain (R group) chemistry H-C-CH₂ NH; Alanine (Ala, A) COO H-C-CH₂-CH ΝΗ; CH3 CH₂ Leucine (Leu, L) COO™ H-C-CH₂- ΝΗ; H Tryptophan (Trp, W) Polar amino acids COO™ H-C-CH₂-OH NH; Serine (Ser, S) COO™ H-C-CH₂-C-NH₂ ΝΗ; Asparagine (Asn, N) COO™ cholenie H-C-CH₂-SH NH; 10 od ng Cysteine (Cys, C) NH Aspartate (Asp, D) COO™ H-C Charged amino acids COO™ H-C-CH₂-C-0- NH; CH₂ Valine (Val. V) COO H-C NH; CH₂ CH Isoleucine (Ile. I) CH₂ -CH-CH₂-CH₂ COO H-C-CH₂ COO NH COO™ CH3 H-C -CH-OH H₂N-CH₂ Proline (Pro, P) NH Threonine (Thr, T) CH₂ H-C-CH₂-CH₂-C-NH₂ COO Glutamine (Gln, Q) COO H-C-H NH Glycine (Gly, G) NH Glutamate (Glu, E) COO™ NH₂ H-C-CH, CH, CH,NH-CNH, ΝΗ; COO™ H-C-CH₂- NH Phenylalanine (Phe, F) H-C-CH₂-CH₂-C-0- COO™ H-C-CH₂-CH₂-5-CH₂ NH; Methionine (Met. M) COO™ H-C-CH₂- NH Tyrosine (Tyr, Y) COO H-C-CH₂- NH H Histidine (His, H) OH COO™ HC—CH, CH, CH,—CH, NH NH Lysine (Lys, K) Arginine (Arg, R) [From Essential Biochemistry 3/e; Pratt, C.W. and Cornely, K.; Copyright © (2013) by John Wiley & Sons, Inc. Reprinted with permission of John Wiley & Sons, Inc.] Critical Thinking Questions: laban 5. Look at the structure of alanine at the top of Model 2. Identify the amino group and the carboxyl group in alanine. Ensure that all team members agree. CA46A

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Chapter1: Chemical Foundations
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Structures and abbreviations of the 20 standard amino acids in
classified according to their side chain (R group) chemistry
form,
Hydrophobic amino acids
COO™
H-C-CH3
NH
Alanine (Ala, A)
Model 2:
witterionic
COO™
H-C-CH₂-CH
NH
CH₂
Leucine (Leu, L)
COO™
Toulon H-C
NH
-CH₂-
Tryptophan (Trp, W)
Table Polar amino acids
COO™
H-C-CH₂-OH
NH
Serine (Ser, S),
COO™
CH3
H-C
CH₂
O
H-C
NH
Asparagine (Asn, N)
COO™
-NH₂
-CH₂-SH
NH
10 xod and Cysteine (Cys, C)
NH
Aspartate (Asp, D)
COO™
H-C
Charged amino acids
COO™
Lo
H-C-CH₂-C-0-
NH
CH₂
aline (Val, V)
COO™
H-C
NH
H-C
CH3
-CH
St
Isoleucine (Ile, I)
-CH-CH₂-CH3
CH₂
COO™ CH3
COO™
CH₂
H-C-
H₂N
-CH₂
Proline (Pro, P)
COO
Houba
NH
Threonine (Thr, T)
CH₂
COO
-CH-OH
H-C-CH₂-CH₂-C-NH₂
ΝΗ;
Glutamine (Gln, Q)
COO
H-C-H
NH
Glycine (Gly, G)
O
Wa
H-C-CH₂-CH₂-C-O
COO™
NH₂
H–C—CH, —CH, —CH, NH—C=NH
ΝΗ;
NH
Glutamate (Glu, E)
COO™
H-C-CH₂-
NH
Phenylalanine (Phe, F)
COO™
H-C-CH₂-CH₂-S-CH₂
NH
Methionine (Met, M)
COO
H-C-CH₂
NH
- 247 -
Tyrosine (Tyr, Y)
COO™
H-C-CH₂
NH
H
Histidine (His, H)
N
-OH
COO
H—C—CH, CH, —CH, —CH, NH
ΝΗ,
Lysine (Lys, K)
D
Arginine (Arg, R)
[From Essential Biochemistry 3/e; Pratt, C.W. and Cornely, K.; Copyright © (2013) by John Wiley & Sons, Inc.
Reprinted with permission of John Wiley & Sons, Inc.]
Critical Thinking Questions:
5. Look at the structure of alanine at the top of Model 2. Identify the amino group and the
carboxyl group in alanine. Ensure that all team members agree.
CA46A
Transcribed Image Text:Structures and abbreviations of the 20 standard amino acids in classified according to their side chain (R group) chemistry form, Hydrophobic amino acids COO™ H-C-CH3 NH Alanine (Ala, A) Model 2: witterionic COO™ H-C-CH₂-CH NH CH₂ Leucine (Leu, L) COO™ Toulon H-C NH -CH₂- Tryptophan (Trp, W) Table Polar amino acids COO™ H-C-CH₂-OH NH Serine (Ser, S), COO™ CH3 H-C CH₂ O H-C NH Asparagine (Asn, N) COO™ -NH₂ -CH₂-SH NH 10 xod and Cysteine (Cys, C) NH Aspartate (Asp, D) COO™ H-C Charged amino acids COO™ Lo H-C-CH₂-C-0- NH CH₂ aline (Val, V) COO™ H-C NH H-C CH3 -CH St Isoleucine (Ile, I) -CH-CH₂-CH3 CH₂ COO™ CH3 COO™ CH₂ H-C- H₂N -CH₂ Proline (Pro, P) COO Houba NH Threonine (Thr, T) CH₂ COO -CH-OH H-C-CH₂-CH₂-C-NH₂ ΝΗ; Glutamine (Gln, Q) COO H-C-H NH Glycine (Gly, G) O Wa H-C-CH₂-CH₂-C-O COO™ NH₂ H–C—CH, —CH, —CH, NH—C=NH ΝΗ; NH Glutamate (Glu, E) COO™ H-C-CH₂- NH Phenylalanine (Phe, F) COO™ H-C-CH₂-CH₂-S-CH₂ NH Methionine (Met, M) COO H-C-CH₂ NH - 247 - Tyrosine (Tyr, Y) COO™ H-C-CH₂ NH H Histidine (His, H) N -OH COO H—C—CH, CH, —CH, —CH, NH ΝΗ, Lysine (Lys, K) D Arginine (Arg, R) [From Essential Biochemistry 3/e; Pratt, C.W. and Cornely, K.; Copyright © (2013) by John Wiley & Sons, Inc. Reprinted with permission of John Wiley & Sons, Inc.] Critical Thinking Questions: 5. Look at the structure of alanine at the top of Model 2. Identify the amino group and the carboxyl group in alanine. Ensure that all team members agree. CA46A
8
6. What is the side chain of alanine (circle one)? methyl
What is the side chain of valine (circle one)? methyl
ethyl
propyl
7.
bonds. Which of the three classes of amino acids (hydrophobic, polar, charged) has the
Examine the side chains of the 20 amino acids, and circle each one that has N-H or O-H
fewest number of amino acids that can hydrogen bond with water?
10. What is the opposite of hydrophobic?
classes of amino acids could you apply this term?
CA46A
9. Examine the structure of tryptophan in Model 2. Discuss with your team and devise an
explanation for why it is considered hydrophobic even though it has an N-H bond.
+H3N.
CH₂
(glycine)
Information:
The carboxylic acid (carboxyl) group of one amino acid and the amino group of another can
undergo a condensation reaction to form a new bond, called a peptide bond. The new
molecule is called a dipeptide. More condensations can lead to tripeptides, tetrapeptides,
etc., and finally to polypeptides.
+H3N.
ethyl
Model 3: The condensation reaction of glycine and alanine makes a dipeptide.
O
CH3
CH
CH3 alanine
+H3N.
propyl
CH₂
glycylalanine
248-
To which of the three
isopropyl
isopropyl
CH
Critical Thinking Questions:
(11.) The a carbons are the ones bonded to both a carbonyl carbon and a nitrogen atom.
Circle all the a carbons in Model 3.
(12. Draw a box around the part of the structure for glycylalanine in Model 3 that originated
in alanine. Draw another box around the part of the structure for glycylalanine in Model
3 that originated in glycine. All the atoms of glycylalanine should now be in one box or
the other.
alanylglycine
+H3N
(13. The new bond that was formed in the condensation reaction that connected glycine to
alanine is called a peptide bond. Draw an arrow to this bond and label it in the model.
(14. Consider the dipeptide Ala-Gly (alanylglycine)
shown at the right. Is this the same molecule
as Gly-Ala (glycylalanine), or are they
isomers? If they are isomers, what type of
isomers are they? (Hint: Look at the
a carbons.)
+ H₂O
CH
CH3
15. Circle the three side chains (R groups) in Model 4 on the following page. What three
amino acids condensed together to make the tripeptide? Label them in the Model.
Transcribed Image Text:8 6. What is the side chain of alanine (circle one)? methyl What is the side chain of valine (circle one)? methyl ethyl propyl 7. bonds. Which of the three classes of amino acids (hydrophobic, polar, charged) has the Examine the side chains of the 20 amino acids, and circle each one that has N-H or O-H fewest number of amino acids that can hydrogen bond with water? 10. What is the opposite of hydrophobic? classes of amino acids could you apply this term? CA46A 9. Examine the structure of tryptophan in Model 2. Discuss with your team and devise an explanation for why it is considered hydrophobic even though it has an N-H bond. +H3N. CH₂ (glycine) Information: The carboxylic acid (carboxyl) group of one amino acid and the amino group of another can undergo a condensation reaction to form a new bond, called a peptide bond. The new molecule is called a dipeptide. More condensations can lead to tripeptides, tetrapeptides, etc., and finally to polypeptides. +H3N. ethyl Model 3: The condensation reaction of glycine and alanine makes a dipeptide. O CH3 CH CH3 alanine +H3N. propyl CH₂ glycylalanine 248- To which of the three isopropyl isopropyl CH Critical Thinking Questions: (11.) The a carbons are the ones bonded to both a carbonyl carbon and a nitrogen atom. Circle all the a carbons in Model 3. (12. Draw a box around the part of the structure for glycylalanine in Model 3 that originated in alanine. Draw another box around the part of the structure for glycylalanine in Model 3 that originated in glycine. All the atoms of glycylalanine should now be in one box or the other. alanylglycine +H3N (13. The new bond that was formed in the condensation reaction that connected glycine to alanine is called a peptide bond. Draw an arrow to this bond and label it in the model. (14. Consider the dipeptide Ala-Gly (alanylglycine) shown at the right. Is this the same molecule as Gly-Ala (glycylalanine), or are they isomers? If they are isomers, what type of isomers are they? (Hint: Look at the a carbons.) + H₂O CH CH3 15. Circle the three side chains (R groups) in Model 4 on the following page. What three amino acids condensed together to make the tripeptide? Label them in the Model.
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