Next Article in Journal
Exploring the Kamchatka Geothermal Region in the Context of Life’s Beginning
Previous Article in Journal
Developmental Biology in Cyanobacteria
Article Menu
Issue 2 (June) cover image

Export Article

Open AccessCommunication

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
  |  
PDF [3078 KB, uploaded 16 May 2019]
  |  

Abstract

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
Figures

Graphical abstract

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).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Life EISSN 2075-1729 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top