The side-chain carboxyl groups of aspartic acid and glutamic acid are often protected as benzyl esters. Me,COČNHCHČOCH3 ВОС as amino- protecting group CH, CH, benzyl ester as carboxyl- protecting group C=0 ÓCH,Ph

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Chapter19: Proteins
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Problem 19.72E: What functional groups are found in all amino acids? How many different amino acids are found in...
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How do you deprotect the side-chain carboxyl under mild conditions without removing the BOC-protecting group at the same time?

The side-chain carboxyl groups of aspartic acid and glutamic acid are often protected as
benzyl esters.
Me,COČNHCHČOCH3
ВОС as amino-
protecting group
CH,
CH,
benzyl ester as carboxyl-
protecting group
C=0
ÓCH,Ph
Transcribed Image Text:The side-chain carboxyl groups of aspartic acid and glutamic acid are often protected as benzyl esters. Me,COČNHCHČOCH3 ВОС as amino- protecting group CH, CH, benzyl ester as carboxyl- protecting group C=0 ÓCH,Ph
Expert Solution
Step 1

The deprotection of the side chain carboxyl group (benzyl ester) can be done by the hydrogenolysis with H2 in presence of a metal catalyst palladium (pd) ) or platinum (pt) under mild conditions. 

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