Peptide formation from aminomalononitrile (HCN trimer)

Moser, Robert E.; Claggett, A.R.; Matthews, Clifford N.

doi:10.1016/s0040-4039(01)99012-4

Cited by 49 publications

(35 citation statements)

References 7 publications

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“…7,11,13,[21][22][23] It is formally a trimer of hydrogen cyanide and spontaneously polymerizes when commercially available p-toluenesulfonate is neutralized (Figure 1b). 24 It allows easy access to HCN polymers under very mild and controllable conditions without the need to use HCN itself. 24,25 The extremely adhesive polymer produced is structurally very complex.…”

Section: Introductionmentioning

confidence: 99%

“…24 It allows easy access to HCN polymers under very mild and controllable conditions without the need to use HCN itself. 24,25 The extremely adhesive polymer produced is structurally very complex. Hydrolysis experiments of the polymers result in the observation of amino acids with particularly significant amounts of glycine and polycyclic nitrogenous compounds such as purines and imidazole derivatives (Supplementary Figure S1).…”

Section: Introductionmentioning

confidence: 99%

“…Hydrolysis experiments of the polymers result in the observation of amino acids with particularly significant amounts of glycine and polycyclic nitrogenous compounds such as purines and imidazole derivatives (Supplementary Figure S1). 9,11,[24][25][26][27][28][29][30] Because of these properties, we investigated the AMN polymer as a candidate for a new generic coating method that may be particularly useful in biomedical applications such as cell culture tools, providing high cell attachment and surface coatings on implantable medical devices providing enhanced tissue integration.…”

Section: Introductionmentioning

confidence: 99%

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Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

et al. 2015

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In the field of prebiotic chemistry, hydrogen cyanide (HCN)-derived polymers have been studied for many years as a possible source of the precursors that provide the building blocks for proteins as well as nucleic acids, and they have also been associated with the origin of life. The HCN trimer, aminomalononitrile (AMN), polymerizes to give a brown complex nitrogenous polymer. We report the one-step polymerization-deposition of AMN as a simple generic surface-coating method and as an application of prebiotic chemical research to material science. We found that this polymerization, carried out in buffered aqueous solutions, can be used to coat a wide range of organic and inorganic substrate materials. The robust, non-cytotoxic coatings also provide for excellent cell attachment, suggesting potential biomedical applications. Furthermore, the coating chemistry allows for the immobilization of other compounds, including metals, both during coating formation or by performing secondary immobilization reactions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

et al. 2015

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“…Besides HCN polymerization, a prebiotically central molecule, or its trimer form leading after hydrolysis to polyglycine (Moser et al 1968), all kinds of polycondensation strategies have been suggested, starting from the free amino acid. Fox and Dose (1977), using molten amino acids in the presence of excess amino acids in their acid or basic form, obtained polymers in which, however, peptide bonds are not the most important.…”

Section: Introductionmentioning

confidence: 99%

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

et al. 1999

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Alpha-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NOx. Nitrosation of solid CAA (glycine or valine derivative) by a 4/1 NO/O2 gaseous mixture (1 atm) yields N-carboxyanhydride (NCA) quantitatively in less than 1 h at room temperature. The crude solid NCA undergoes quantitative oligomerization (from trimer to nonamer under the conditions we used) when treated with a (bi)carbonate aqueous buffer at pH 9. We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario).

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“…Moser et al (1968) (one of the co-authors was Clifford Matthews) reported a "peptide synthesis" using the HCN trimer aminomalonitrile, after pre-treatment in the form of a mild hydrolysis. Matthews remained true to HCN chemistry, which is indeed an attractive research area.…”

Section: Hydrogen Cyanide and Its Derivativesmentioning

confidence: 99%

Chemical Evolution and the Origin of Life

Rauchfuss¹

2008

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-The f omation of more complex carbon compounds from simple ones through t h e action of radiation i s used i n an interpretation of the original formation of such compounds on earth, The relation of plants and animals and evolution of photosynthesis i s ?iscussed i n the l i g h t of the p r t i c ip t i o n of sulfur compounds i n the metabolism of both g r o u p , (' 1 The work described i n t h i s pipr was sponsorer? by the U. S. At-c Energy 2 . d s s f on,

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Peptide formation from aminomalononitrile (HCN trimer)

Cited by 49 publications

References 7 publications

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

Chemical Evolution and the Origin of Life

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