Biomimetic synthesis of esters of natural amino acids

Ribozymomimetic Chemical Synthesis of Peptide Bond Using Phosphorous Acid/Oxirane Mediators

“…[19][20][21] In those cases, N-functional group protection and C-functional group activation was achieved in situ during the condensation reaction. The activation of α-carboxyl function as an electrophile occurred at the same time as α-amino group protection, which ensures that only the condensation reaction leading to the target takes place.…”

“…H-Phe-OMe was obtained using the same methodology described by Devedjiev and colleagues. [19][20][21] HGly-NH 2 was purchased from IRIS-Biotech. H 3 PO 3 , propylene oxide, and isobutylene oxide (2,2-dimethyl oxirane, also named 1,1-dimetyl ethylene oxide) were purchased from Merck.…”

A Novel General Methodology for Ribozyme-Mimetic Synthesis of Methyl Esters of Various Natural Amino Acids, Simulating the Prebiotic Biomolecule Creation

“…In this way (according to this procedure) the reaction successfully proceeds only between the α-carboxyl group, and with other nucleophile, for instance: alcohol, amine, or ester (amide) of the amino acid (C-end protected). Our previous experiments show, that in the presence of methanol as the simplest nucleophile, methyl esters of amino acids were prepared successfully, as the first prepared methyl esters were of the following amino acids: Phe, Thr, Gly, Ala [23,24]. Thus, by our originally developed procedure, methyl esters of a variety of amino acids were synthesized.…”

“…This allowed us to improve the methodology of inter bio monomeric bond formation, by the using of the more inexpensive methyl oxirane (propylene oxide) as condensing reagent, and phosphonic (phosphorous) acid -for the functional group influence (amino group protection and at the same time carboxyl functionality activation), thus avoiding the addition stage of the alpha-amino group protection. Our previous studies and results on the reaction of amino acid esters preparation catalyzed by phosphorous acid/oxirane analogues allowed us to synthesize a series of methyl esters of amino acids, as well as amides, starting from the corresponding free analogues [23][24][25]. Their N-functional group protection and C-functional group activation were realized in situ during the condensation reaction.…”

“…In this article, we demonstrate the synthesis of methyl esters of various natural amino acids, using bio-mimetic reaction, which resembles and tries to prove the ribozyme function and role of RNA as an enzyme at the Early Ages of Earth Evolution (Figure 1). *The methyl esters of Gly, L-Ala, L-Phe and L-Thr were previously synthesized by the author and coworkers [23,24].…”