Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions
The origin of biopolymers is a central question in origins of life research. In extant life, proteins are coded linear polymers made of a fixed set of twenty alpha-<sub>L</sub>-amino acids. It is likely that the prebiotic forerunners of proteins, or protopeptides, were more heterogenous...
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MDPI AG
2022-02-01
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| Online Access: | https://www.mdpi.com/2075-1729/12/2/265 |
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| author | Moran Frenkel-Pinter Kaitlin C. Jacobson Jonathan Eskew-Martin Jay G. Forsythe Martha A. Grover Loren Dean Williams Nicholas V. Hud |
| author_facet | Moran Frenkel-Pinter Kaitlin C. Jacobson Jonathan Eskew-Martin Jay G. Forsythe Martha A. Grover Loren Dean Williams Nicholas V. Hud |
| author_sort | Moran Frenkel-Pinter |
| collection | DOAJ |
| description | The origin of biopolymers is a central question in origins of life research. In extant life, proteins are coded linear polymers made of a fixed set of twenty alpha-<sub>L</sub>-amino acids. It is likely that the prebiotic forerunners of proteins, or protopeptides, were more heterogenous polymers with a greater diversity of building blocks and linkage stereochemistry. To investigate a possible chemical selection for alpha versus beta amino acids in abiotic polymerization reactions, we subjected mixtures of alpha and beta hydroxy and amino acids to single-step dry-down or wet-dry cycling conditions. The resulting model protopeptide mixtures were analyzed by a variety of analytical techniques, including mass spectrometry and NMR spectroscopy. We observed that amino acids typically exhibited a higher extent of polymerization in reactions that also contained alpha hydroxy acids over beta hydroxy acids, whereas the extent of polymerization by beta amino acids was higher compared to their alpha amino acid analogs. Our results suggest that a variety of heterogenous protopeptide backbones existed during the prebiotic epoch, and that selection towards alpha backbones occurred later as a result of polymer evolution. |
| first_indexed | 2024-03-09T21:34:35Z |
| format | Article |
| id | doaj.art-b72948f0feba4f9bbc863250f99e04f8 |
| institution | Directory Open Access Journal |
| issn | 2075-1729 |
| language | English |
| last_indexed | 2024-03-09T21:34:35Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Life |
| spelling | doaj.art-b72948f0feba4f9bbc863250f99e04f82023-11-23T20:46:41ZengMDPI AGLife2075-17292022-02-0112226510.3390/life12020265Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis ReactionsMoran Frenkel-Pinter0Kaitlin C. Jacobson1Jonathan Eskew-Martin2Jay G. Forsythe3Martha A. Grover4Loren Dean Williams5Nicholas V. Hud6NSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USANSF-NASA Center for Chemical Evolution, Georgia Institute of Technology, Atlanta, GA 30332, USAThe origin of biopolymers is a central question in origins of life research. In extant life, proteins are coded linear polymers made of a fixed set of twenty alpha-<sub>L</sub>-amino acids. It is likely that the prebiotic forerunners of proteins, or protopeptides, were more heterogenous polymers with a greater diversity of building blocks and linkage stereochemistry. To investigate a possible chemical selection for alpha versus beta amino acids in abiotic polymerization reactions, we subjected mixtures of alpha and beta hydroxy and amino acids to single-step dry-down or wet-dry cycling conditions. The resulting model protopeptide mixtures were analyzed by a variety of analytical techniques, including mass spectrometry and NMR spectroscopy. We observed that amino acids typically exhibited a higher extent of polymerization in reactions that also contained alpha hydroxy acids over beta hydroxy acids, whereas the extent of polymerization by beta amino acids was higher compared to their alpha amino acid analogs. Our results suggest that a variety of heterogenous protopeptide backbones existed during the prebiotic epoch, and that selection towards alpha backbones occurred later as a result of polymer evolution.https://www.mdpi.com/2075-1729/12/2/265prebiotic chemistrycondensation dehydrationpeptide evolutionchemical evolutiondepsipeptides |
| spellingShingle | Moran Frenkel-Pinter Kaitlin C. Jacobson Jonathan Eskew-Martin Jay G. Forsythe Martha A. Grover Loren Dean Williams Nicholas V. Hud Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions Life prebiotic chemistry condensation dehydration peptide evolution chemical evolution depsipeptides |
| title | Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions |
| title_full | Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions |
| title_fullStr | Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions |
| title_full_unstemmed | Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions |
| title_short | Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions |
| title_sort | differential oligomerization of alpha versus beta amino acids and hydroxy acids in abiotic proto peptide synthesis reactions |
| topic | prebiotic chemistry condensation dehydration peptide evolution chemical evolution depsipeptides |
| url | https://www.mdpi.com/2075-1729/12/2/265 |
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