The word “isosteric” means having the same general three-dimensional shape. a. Look up amino acid structures. Find an amino acid side chain that is isosteric with a valine side chain. (Hint: hydrogen atoms are small, so while they of course affect molecular geometry, what matters more is the molecular geometry of non-hydrogen atoms connected to other non-hydrogen atoms.) Draw both side chains and label the molecular geometry around each non-hydrogen atom

Organic Chemistry
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Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter25: Carbohydrates
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Problem 25.48P
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The word “isosteric” means having the same general three-dimensional shape.
a. Look up amino acid structures. Find an amino acid side chain that is isosteric with a valine side chain. (Hint: hydrogen atoms are small, so while they of course affect molecular geometry, what matters more is the molecular geometry of non-hydrogen atoms connected to other non-hydrogen atoms.) Draw both side chains and label the molecular geometry around each non-hydrogen atom.

H.
CH3
H3N
co2
co
H3N
co
co
Alanine
Valine
Leucine
Glycine
Gly, G
Ala, A
Val, V
Leu, L
H
HO.
co
co
co
co
Phenylalanine
Phe, F
Tyrosine
Туг, Y
Tryptophan
Trр, W
Isoleucine
Ile, I
CH3
SH
но.
CH3
но
H3N
co
H3N
co
co
co
Cysteine
Cys, C
Threonine
Thr, T
Serine
Methionine
Met, M
Ser, S
H
H2N
`NH
N°
®NH2
CO2
co
co
H3N
co
Proline
Histidine
Arginine
Arg, R
Lysine
Lys, K
Pro, P
His, H
H2N.
`NH2
H3N'
co
H3N
co
H3Ñ
co
H3N
co
Aspartate
Asp, D
Asparagine
Asn, N
Glutamate
Glutamine
Glu, E
Gln, Q
Transcribed Image Text:H. CH3 H3N co2 co H3N co co Alanine Valine Leucine Glycine Gly, G Ala, A Val, V Leu, L H HO. co co co co Phenylalanine Phe, F Tyrosine Туг, Y Tryptophan Trр, W Isoleucine Ile, I CH3 SH но. CH3 но H3N co H3N co co co Cysteine Cys, C Threonine Thr, T Serine Methionine Met, M Ser, S H H2N `NH N° ®NH2 CO2 co co H3N co Proline Histidine Arginine Arg, R Lysine Lys, K Pro, P His, H H2N. `NH2 H3N' co H3N co H3Ñ co H3N co Aspartate Asp, D Asparagine Asn, N Glutamate Glutamine Glu, E Gln, Q
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