Thioester

General structure of a thioester

A thioester is a molecule with a group C-S-CO-C. They are like esters, but with a sulfur atom instead of an oxygen one. Like esters, they can be made from carboxylic acids. In the synthesis, a thiol is used instead of an alcohol.

Thioesters are very important in biochemistry. They are made in the body during reactions that make fatty acids. They are also important intermediates in the production of ATP, which is the molecule that gives energy to the body.

In chemistry, thioesters can be also used as electrophiles. They are more reactive than esters and amides. They can also do aldol reactions.

Thioester Media

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  Formation of amides from thioesters

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  Fukuyama coupling

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  Thioesters are components of the native chemical ligation method for peptide synthesis.

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  Structure of acetyl coenzyme A, a thioester that is a key intermediate in the biosynthesis of many biomolecules.

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  General structure of a thionoester, where R and R' are organyl groups, or H in the case of R

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  Skeletal formula of methyl thionobenzoate

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  Thionoester-from-thioacyl-chloride-2D-skeletal

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  Transesterification of Thionoesters