Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth?
Unlike its shorter analog, cysteine, and its methylated derivative, methionine, homocysteine is not today a proteinogenic amino acid. However, this thiol containing amino acid is capable of forming an activated species intramolecularly. Its thiolactone could have made it an interesting molecular bui...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-04-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/12/4/555 |
| _version_ | 1797436686713487360 |
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| author | Sparta Youssef-Saliba Anne Milet Yannick Vallée |
| author_facet | Sparta Youssef-Saliba Anne Milet Yannick Vallée |
| author_sort | Sparta Youssef-Saliba |
| collection | DOAJ |
| description | Unlike its shorter analog, cysteine, and its methylated derivative, methionine, homocysteine is not today a proteinogenic amino acid. However, this thiol containing amino acid is capable of forming an activated species intramolecularly. Its thiolactone could have made it an interesting molecular building block at the origin of life on Earth. Here we study the cyclization of homocysteine in water and show theoretically and experimentally that in an acidic medium the proportion of thiolactone is significant. This thiolactone easily reacts with amino acids to form dipeptides. We envision that these reactions may help interpret why a methionine residue is introduced at the start of all protein synthesis. |
| first_indexed | 2024-03-09T11:06:09Z |
| format | Article |
| id | doaj.art-7370da1bb08e4ddba2a13bb13dd3fc13 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-09T11:06:09Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-7370da1bb08e4ddba2a13bb13dd3fc132023-12-01T00:56:47ZengMDPI AGBiomolecules2218-273X2022-04-0112455510.3390/biom12040555Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth?Sparta Youssef-Saliba0Anne Milet1Yannick Vallée2University Grenoble Alpes, CNRS, DCM, F-38058 Grenoble, FranceUniversity Grenoble Alpes, CNRS, DCM, F-38058 Grenoble, FranceUniversity Grenoble Alpes, CNRS, DCM, F-38058 Grenoble, FranceUnlike its shorter analog, cysteine, and its methylated derivative, methionine, homocysteine is not today a proteinogenic amino acid. However, this thiol containing amino acid is capable of forming an activated species intramolecularly. Its thiolactone could have made it an interesting molecular building block at the origin of life on Earth. Here we study the cyclization of homocysteine in water and show theoretically and experimentally that in an acidic medium the proportion of thiolactone is significant. This thiolactone easily reacts with amino acids to form dipeptides. We envision that these reactions may help interpret why a methionine residue is introduced at the start of all protein synthesis.https://www.mdpi.com/2218-273X/12/4/555prebiotic chemistryabiogenesishomocysteinethiolactonepeptides |
| spellingShingle | Sparta Youssef-Saliba Anne Milet Yannick Vallée Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? Biomolecules prebiotic chemistry abiogenesis homocysteine thiolactone peptides |
| title | Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? |
| title_full | Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? |
| title_fullStr | Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? |
| title_full_unstemmed | Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? |
| title_short | Did Homocysteine Take Part in the Start of the Synthesis of Peptides on the Early Earth? |
| title_sort | did homocysteine take part in the start of the synthesis of peptides on the early earth |
| topic | prebiotic chemistry abiogenesis homocysteine thiolactone peptides |
| url | https://www.mdpi.com/2218-273X/12/4/555 |
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