Chiral Sugars Drive Enantioenrichment in Prebiotic Amino Acid Synthesis
Open accessAbstract
Chiral pentose sugars mediate the enantioselective synthesis of amino acid precursors, with the magnitude of the chiral induction dictated by a subtle cooperativity between sugar hydroxyl groups. Ribose and lyxose give opposite chiral preferences, and theoretical calculations reveal the pseudoenantiomeric nature of transition state structures from the two sugars. Prebiotically plausible mixtures of natural d-sugars lead to enantioenrichment of natural l-amino acid precursors. Temporal monitoring and kinetic modeling of the reaction reveal an unusual dynamic kinetic resolution that shifts toward an enantioselective pathway over time, providing an amplification mechanism for the transfer of chiral information. This work adds to growing evidence for synergy in the etiology of the single chirality of the two most important classes of biological molecules, the sugars that make up DNA and RNA and the amino acids that form proteins.
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D-ribose provided the product with 70% e.e. biased in favour of unnatural (R)-configuration.
“Notably, D-ribose provided the product with 70% e.e. biased in favour of unnatural (R)-configuration (Fig. 20, ( 5)).”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [515]
The discussion of Table 5 (indexed under Abstract; page unavailable) identifies the major product of the d-ribose-mediated reaction as the R aminoamide. The copy’s Table 1 passage describes enantiomeric-excess measurements, but its numerical results are absent, so the specific 70% e.e. is not supported by the available text. (LLM, conf=0.85)
Experimental — accuracy not yet measuredThe mixture of four D-pentoses favoured the natural (S) amino acid precursor.
“the mixture of four D-pentoses actually favoured the natural (S) amino acid precursor.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [515]
Hydrolysis of 2-benzyl a-amino nitrile yielded the corresponding a-amino amide (precursor of phenylalanine) with various e.e. values and configurations depending on the nature of the sugars.
“The hydrolysis of 2-benzyl a-amino nitrile yielded the corresponding a-amino amide (precursor of phenylalanine) with various e.e. values and configurations depending on the nature of the sugars.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [515]
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Li, L., Li, G., Xie, H., & Zhang, Z. (2024) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2024.124428 · Cited by 1
A Continuing Career in Physical Organic Chemistry: Donna G. Blackmond
Ji, Y., Otte, D. A. L., & Ruck, R. T. (2023) · ACS Catalysis · doi:10.1021/acscatal.3c04565
Mirror-image Biological Molecules
Chen, J., & Zhu, T. F. (2021) · Chinese Journal of Space Science · doi:10.11728/cjss2021.01.141
(2019) · Elsevier eBooks · doi:10.1016/b978-0-12-812212-9.16001-4
- Authors
- Wagner, A. J., Zubarev, D. Y., Aspuru-Guzik, A., & Blackmond, D. G.
- Affiliations
- Scripps Research Institute (US)
- Harvard University (US)
- Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States
- Corresponding author
- Blackmond, Donna G.
- Venue
- ACS Central Science
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-03-21
- Volume
- 3
- Issue
- 4
- Pages
- 322-328
- ISSN
- 2374-7943 (ISSN-L)
- 2374-7951
- PMC
- PMC5408343
- OpenAlex
- W2600935015
- Cited by
- 52
- References
- 57
- Citations by year
- 2026: 1 · 2025: 4 · 2024: 6 · 2023: 5 · 2022: 4 · 2021: 7 · 2020: 3 · 2019: 8 · 2018: 10 · 2017: 4
- FWCI
- 3.74
- Type
- journal article
- Language
- en
- Open access
- diamond
- doi.org
- Licence
- Locations
- ACS Central Science (publishedVersion, other-oa)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Digital Access to Scholarship at Harvard (DASH) (Harvard University) (submittedVersion, cc-by)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- Simons Foundation (SCOL 287625, SCOL 291937)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Enzyme Catalysis and Immobilization
- Keywords
- enantioenrichment, ribose, lyxose, chiral induction, dynamic kinetic resolution, asymmetric synthesis, transition state structure, kinetic modeling, origin of homochirality, amino acid precursors
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