556-33-2Relevant articles and documents
Fowden,Smith
, p. 1043 (1969)
Pagenkopf,Margerum
, p. 501 (1968)
Influence de composes a heterocycle azote et particulierement d'azoles non condenses sur des reactions "prebiotiques" de condensation d'acides α-amines induites par les polyphosphates an milieu aqueux
Rabinowitz, Joseph,Hampai, Aioub
, p. 962 - 966 (1980)
In previous experiments aqueous solutions of α-aminoacids in the presence of cyclic or linear polyphosphates, pH range 7-11, yielded up to 40percent of dipeptide but only 0.3-0.5percent of tripeptide .By addition of imidazole the yield of tripeptide could be increased about ten times .Therefore, we have studied for the condensation reaction of glycine the influence of the addition to aqueous solutions 0.1M in glycine and 0.1M in trimethaphosphate at room temperature, pH range 6.7-8.9, of several azoles (pyrrole, pyrazole, imidazole, 1,2,4-triazole and tetrazole), of adenine, guanine, uracil, cytosine, and of several nucleosides (adenosine, guanoside, uridine and cytydine).Among the produts studied, only 1,2,4-triazole and imidazole improve appreciably, by a factor of about 15, the yield of triglycine (up to 7.8percent).While it is very likely that imidazole has played an important role during prebiotic chemical evolution, it is not clear at present whether 1,2,4-triazole has a prebiotic significance.
Harada et al.
, p. 1752 (1972)
Mechanochemical Prebiotic Peptide Bond Formation**
Cindro, Nikola,Grube?i?, Sa?a,Hernández, José G.,Me?trovi?, Ernest,Stolar, Tomislav,U?arevi?, Krunoslav
supporting information, p. 12727 - 12731 (2021/05/07)
The presence of amino acids on the prebiotic Earth, either stemming from endogenous chemical routes or delivered by meteorites, is consensually accepted. Prebiotically plausible pathways to peptides from inactivated amino acids are still unclear as most oligomerization approaches rely on thermodynamically disfavored reactions in solution. Now, a combination of prebiotically plausible minerals and mechanochemical activation enables the oligomerization of glycine at ambient temperature in the absence of water. Raising the reaction temperature increases the degree of oligomerization concomitantly with the formation of a commonly unwanted cyclic glycine dimer (DKP). However, DKP is a productive intermediate in the mechanochemical oligomerization of glycine. The findings of this research show that mechanochemical peptide bond formation is a dynamic process that provides alternative routes towards oligopeptides and establishes new synthetic approaches for prebiotic chemistry.
Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids
Furukawa, Shinya,Fukuyama, Takahide,Matsui, Akihiro,Kuratsu, Mai,Nakaya, Ryotaro,Ineyama, Takashi,Ueda, Hiroshi,Ryu, Ilhyong
supporting information, p. 11980 - 11983 (2015/08/18)
A general method for the synthesis of dipeptides has been developed, which does not require any coupling reagents. This method is based on the reaction of readily available HCl salts of amino acid methyl esters with tetrabutylphosphonium amino acid ionic liquids. The isolation procedure of stepwise treatment with AcOH is easy to carry out. The method was extended to the synthesis of tripeptide, tyrosyl-glycyl-glycine, present in IMREG-1, also.
