Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures
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GCA undergoes the Strecker reaction in excellent yield to afford a stable aminonitrile product, Ser-CN.
“This is in stark contrast to GCA, which undergoes the Strecker reaction in excellent yield to afford a stable aminonitrile product, Ser-CN (fig. S2) (23, 24).”
From Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water (2020) · cites this paper as [23]
Table 1 in the Discussion reports a >95% isolated yield of the serine aminonitrile 13a, supporting the excellent-yield claim. Its caption specifies formation by equilibrating a glycolaldehyde-derived aminal with cyanide and ammonia, rather than demonstrating a direct Strecker reaction of GCA. The passages do not establish that the aminonitrile is stable. (LLM, conf=0.84)
Experimental — accuracy not yet measuredA difficulty in merging formaldehyde and HCN chemistries is possible intramolecular imidolactone formation by larger cyanohydrins, which conduces to their consumption and hydrolysis into homologous carboxylic acids.
“Other difficulty that arise in this context is the possible intramolecular imidolactone formation (10) by larger cyanohydrins (from parent triose, tetrose and pentose sugars; e.g., 9), which conduces to their consumption and hydrolysis into the homologous carboxylic acids (12) (Scheme 7, inbox).97”
From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [97]
The ‘Prebiotic selection of proteinogenic amino acids’ section (page unavailable) reports that cyanide converts glyceraldehyde- and tetrose-derived aminals to cyanohydrins and that rapid imidolactone formation prevents the corresponding aminonitriles from forming. It does not describe this as a difficulty in merging formaldehyde and HCN chemistries, extend the finding to pentose-derived cyanohydrins, or report hydrolysis to homologous carboxylic acids. (LLM, conf=0.82)
Experimental — accuracy not yet measuredGlycolaldehyde and glyceraldehyde can react with 2-aminothiazole to give the corresponding aminals, which selectively precipitate to give crystalline reservoirs of these key intermediates.
“However, glycolaldehyde and glyceraldehyde can react with 2-aminothiazole to give the corresponding aminals, which selectively precipitate to give crystalline reservoirs of these key intermediates (Islam et al. 2017).”
From Protocells and RNA Self-Replication (2018) · cites this paper as Islam et al. 2017
The cyanosulfidic scenario relies on formaldehyde and HCN to produce glyconitrile, plus schreibersite, hydrosulfide, copper and UV light to promote homologation to higher cyanohydrins.
“This scenario relies on two main monomers, formaldehyde and HCN, to produce glyconitrile, plus the action of schreibersite ((Fe, Ni) 3P), hydrosulfide (HS−) as reducing agent, copper and ultraviolet light, to promote the homologation to higher cyanohydrins”
From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [97]
The section on selective extraction of glycolaldehyde and glyceraldehyde discusses sugar separation in a cyanosulfidic environment, not the proposed route from formaldehyde and HCN to glyconitrile and higher cyanohydrins. Searches for glyconitrile, homologation, schreibersite, hydrosulfide, copper, and UV light found no passage in our copy describing the claimed sequence. (LLM, conf=0.75)
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- Authors
- Islam, S., Bučar, D.-K., & Powner, M. W.
- Affiliations
- University College London (GB)
- Corresponding author
- Powner, Matthew W.
- Venue
- Nature Chemistry
- Published
- 2017-01-16
- Volume
- 9
- Issue
- 6
- Pages
- 584-589
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- OpenAlex
- W2578576796
- Cited by
- 115
- References
- 36
- Citations by year
- 2026: 7 · 2025: 10 · 2024: 7 · 2023: 17 · 2022: 11 · 2021: 11 · 2020: 15 · 2019: 13 · 2018: 11 · 2017: 13
- FWCI
- 7.78
- Type
- journal article
- Language
- en
- Open access
- green
- kclpure.kcl.ac.uk
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemistry (publishedVersion)
- Research Portal (King's College London) (submittedVersion)
- UCL Discovery (University College London) (submittedVersion)
- Funders
- Leverhulme Trust
- Engineering and Physical Sciences Research Council (EP/K004980/1)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- prebiotic synthesis, proteinogenic amino acids, nucleotide synthesis, ribonucleotide synthesis, 2-aminothiazole, glycolaldehyde, glyceraldehyde, dihydroxyacetone, isomerization, sugar purification, amino acid selection, origin of life, origin of metabolism
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