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Chemistry of Homocysteine Thiolactone in A Prebiotic Perspective

CNRS, Département de Chimie Moléculaire, Univ. Grenoble Alpes, Campus, F-38058 Grenoble, France
Author to whom correspondence should be addressed.
Received: 17 April 2019 / Revised: 14 May 2019 / Accepted: 14 May 2019 / Published: 16 May 2019
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Homocysteine is a non-proteinogenic sulfur-containing amino acid. Like cysteine, it can form disulfide bridges and complex metallic cations. It is also closely related to methionine, the first amino acid in the synthesis of all contemporary proteins. Furthermore, its cyclized form, a five-membered ring thiolactone, is stable in acidic and neutral water. Here, we demonstrate that this thiolactone may have been formed in the primitive ocean directly from the Strecker precursor of homocysteine, an aminonitrile. Even though it is poorly reactive, this thiolactone may be open by some amines, yielding amides which, in turn, could be the precursors of longer peptides. View Full-Text
Keywords: origin of life; prebiotic chemistry; thioester world; amino acids; homocysteine origin of life; prebiotic chemistry; thioester world; amino acids; homocysteine

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Shalayel, I.; Vallée, Y. Chemistry of Homocysteine Thiolactone in A Prebiotic Perspective. Life 2019, 9, 40.

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