НООССH-CHCOOН + Н,О. H,SO, - HOOCCH,CH(OH)COOH This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion, also known as fumarate, and produces only the (S)-2-hydroxysuccinate enantiomer,also known as (S)-malate. fumarase fumarate + H,O • • (S)-malate Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions. Clearly draw a wedged bond, a dashed bond and two in-plane bonds for the chiral carbon.

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Chapter1: Chemical Foundations
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H,SO,
HOOCCH,CH(OH)COOH
НООССH-CHCOOН + Н,О
This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral
solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific
enzyme fumarase that utilizes only the trans form of 2-butenedioate ion, also known as fumarate, and produces only the
(S)-2-hydroxysuccinate enantiomer,also known as (S)-malate.
fumarase
fumarate + H,O
(S)-malate
Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to
include all hydrogen atoms and show the carboxylates as anions. Clearly draw a wedged bond, a dashed bond and two
in-plane bonds for the chiral carbon.
Draw (S)-malate or (S)-2-hydroxysuccinate
Draw fumarate or trans-2-butenedioate.
H
H.
H
он
Incorrect
Transcribed Image Text:H,SO, HOOCCH,CH(OH)COOH НООССH-CHCOOН + Н,О This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion, also known as fumarate, and produces only the (S)-2-hydroxysuccinate enantiomer,also known as (S)-malate. fumarase fumarate + H,O (S)-malate Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions. Clearly draw a wedged bond, a dashed bond and two in-plane bonds for the chiral carbon. Draw (S)-malate or (S)-2-hydroxysuccinate Draw fumarate or trans-2-butenedioate. H H. H он Incorrect
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