Abstract
The non-enzymatic synthesis of N-benzyloxycarbonyl-L-phenylalanyl-L-leucine (Cbz-Phe-Leu) from lipophilic N-benzyloxycarbonyl-L-phenylalanine (Cbz-Phe) and hydrophilic L-leucine (Leu), by N, N’-dicyclohexylcarbodiimide (DCC) as a condensing agent, was carried out using a reversed micellar system composed of bis(2-ethylhexyl) sodium sulfosuccinate (AOT) as a surfactant and isooctane. We successfully synthesized Cbz-Phe-Leu in a short time and investigated the effects of its operational conditions, the DCC concentration, w0, and the pH on the kinetic parameters and the maximum yields. For dipeptide synthesis, we had to add an excess of DCC with the substrates because of the side reactions of Cbz-Phe. From the pH dependency of the reactivity, a partially cationic form of Leu was better for a synthesis reaction because of the enrichment of Leu at the interface by anionic AOT. The optimum water content on the dipeptide synthesis was w0 = 28 due to the competition of the peptide synthesis and the side reactions. The maximum yield of Cbz-Phe-Leu was 0.565 at 80 h under optimum experimental conditions.
Highlights
Some kinds of proteins, poly and oligopeptides, and amino acids have demonstrated positive health influences and provide numerous potential physiological functions
Dipeptides syntheses are categorized into three methods: chemical, chemoenzymatic, and enzymatic [1]
The expression of enzymes, which catalyze the formation of the peptide bond without protecting the amino acids, are found in gene-modified microbes
Summary
Poly and oligopeptides, and amino acids have demonstrated positive health influences and provide numerous potential physiological functions. In chemical synthesis, including solid-phase peptide synthesis, its cost is relatively high and a harmful reagent is sometimes needed, it has the following advantages: every kind of dipeptide can be synthesized, the yield is usually high, and the procedure is simple [2] They require fully protected peptides, which are difficult to dissolve into an aqueous solution due to their hydrophobicity. Many studies have investigated the chemoenzymatic method using hydrolytic enzymes [2] This method has advantages, including high stereoselectivity and mild reaction conditions, it requires protected amino acids to form desired peptide bonds and suffers from a hydrophobicity problem [1]. Iwn ethsiys nptahpeesri,zwede snyonnth-eenszizyemdantoicna-lelnyzlyipmoapthicialilclyClibpzo-pPhhieli-cLCeubzf-rPohme-lLipeuo-from lipophilic philic protectepdroatmecitneodaacmidi,nCobazc-iPdh, Ce,bazn-Pdhhey, danrodphhyildicrofrpeheilaicmfirneoe acmidin, oLeauci,do,rLperuo,toecrtpedrotected amino amino acid, Leauci-dN, HLe2uu-sNinHg2aurseinvegraserdevmeriscedllamr iscyesltlaermsycsotmempocsoemdpoofsDedCCof, DACOCT, AanOdTi,saon-d isooctane in octane in a shaorsthtoirmt etimbye rbeyprleapcilnagcinLgeuL-eOuM-OeMweitwhitLheLueaunadnLdeLue-uN-HN2Ha2nadnditsitksiknienteicticbeb-ehaviors were haviors were iinnvveessttiiggaatteedd..WWeeeexxaammiinneeddththeeeeffefeccttooffththeeooppereartaitoionnalacl ocnonddititoinons,st,htehemmoloalrar ratio, w0, of ratio, w0, of wawteartesrosluolbuilbiizleizdedwwithitihninthtehreerveevresresdedmmiceiclelellsetsotothtehaemamouonutnotfotfhtehesusrufrafcatcatnatnt present, the present, the ppHHoof fththeewwaateterrccoorree,,aannddtthheeDDCCCC ccoonnccentration in the dipeptidee ssyynntthheessiisson the kinetic on the kinetipc apraamraemteertserasndanthde tmheaxmimauxmimyuimeldysi.eFldigsu. rFei1gushreow1ssthhoewscshethmeatsicchreempraetsicentation of the repre-sentatioCnbozf-tPhheeC-Lbezu-Pshyen-tLheeusissnwthitehsiins rweivtehrisnerdemveircseeldlesm. icelles
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