Lysozyme    is    an    enzyme    that    hydrolyzes    bacterial    cell    wall    polysaccharides.        When     this    reaction    is    carried    out    in    the    presence    of    H218O,    it    is    observed    that    there    is     retention    of    configuration    at    the    C1    carbon    of    the    D    site    sugar    as    shown    below   Two    key    amino    acid    side    chains    (an    Asp    and    a    Glu)    essential    for    lysozyme’s     catalytic    activity    are    positioned    above    and    below    the    C1-O    bond    that    is     cleaved    as    shown    below.        Suggest    a    plausible    mechanism    for    the    reaction    that     starts    with a    nucleophilic    attack    at    C1.

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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 Lysozyme    is    an    enzyme    that    hydrolyzes    bacterial    cell    wall    polysaccharides.        When    
this    reaction    is    carried    out    in    the    presence    of    H218O,    it    is    observed    that    there    is    
retention    of    configuration    at    the    C1    carbon    of    the    D    site    sugar    as    shown    below

 

Two    key    amino    acid    side    chains    (an    Asp    and    a    Glu)    essential    for    lysozyme’s    
catalytic    activity    are    positioned    above    and    below    the    C1-O    bond    that    is    
cleaved    as    shown    below.        Suggest    a    plausible    mechanism    for    the    reaction    that    
starts    with a    nucleophilic    attack    at    C1.

Glu 35
HO
RO-NAG-O
'RO
ACHN
HO-
Asp 52
OH
NHAC
NAM-OR
Transcribed Image Text:Glu 35 HO RO-NAG-O 'RO ACHN HO- Asp 52 OH NHAC NAM-OR
D site
D site
18 OH
+
E site
-H₂O
HO
E site
Transcribed Image Text:D site D site 18 OH + E site -H₂O HO E site
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Is the NAM in the explanation supposed to be NAG as shown above in the illustration?

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