Peptide Synthesis from Hydrogen Cyanide and Water

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

“…20 AMN, along with iminoacetonitrile, has received attention as an intermediate in the polymerization of hydrogen cyanide as well as a highly reactive synthon in heterocyclic organic synthesis. 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.…”

“…Matthew's and Ferris' separate studies of HCN polymerization chemistry, as well as Sagan's and Khare's study of tholins, also involved the facile production of complex, highly colored organic polymers. [7][8][9][10][11][12][13][14][15] They have also been considered as a potential source of amino acids, nucleobases and peptides on earth and appear to be common throughout our solar system. For example, these materials have been proposed to be the source of the distinctive orange, redbrown and black colors of comets and the atmosphere of planets and moons such as Saturn, Jupiter and Titan and carbonaceous meteorites, indicating their abundance in our solar system and the universe, respectively.…”

Special Issue: Abstracts From the 2008 Issol Meeting

“…Ferris et al 1973, Voet and Schwartz 1983. However, in spite of the many efforts made to elucidate their structure and of the proposed models (Umemoto et al 1987, Ferris et al 1981, Matthews and Moser 1967and Völker 1960) some questions are still opened. Since these studies, experimental analytical techniques have advanced enormously.…”

Hydrogen cyanide polymers connect cosmochemistry and biochemistry

“…There are two major problems with monomers: 1) they are water soluble and would be infinitely dilute in the primitive ocean; 2) condensing the amino acids or nucleobases into polymers with catalytic or informational capabilities would be virtually impossible in the watery ocean environment. Matthews & Moser (1967) showed that water is not required initially to form amino acids, as it would be if the Strecker route was involved. When methane and ammonia (or nitrogen) are sparked in the absence of water, hydrogen cyanide and acetylene are formed and both polymerize, the acetylene yielding primarily hydrocarbons and PAHs and the HCN yielding primarily HCN polymer (see Figure 1).…”

“…These solutions must also contain higher molecular weight macromolecules because on further hydrolysis by heating in acid or base (6N HCl 24 hr at 110 • or pH 8 phosphate buffer, 140 • , 3 days) greatly increased types and quantities of amino acids and nucleobases are detected. Glycine is the major amino acid produced (1 to 9%) with lesser amounts of alanine, aspartic acid, glutamic acid and several other amino acids (Matthews & Moser 1966, 1967. The nucleobases adenine, guanine, uracil and eight others were identified from the hydrolysis of solids produced in a dilute aqueous NH 4 CN solution frozen at -78 • C for 27 years (Miyakawa et al 2002).…”