Optimized enzymatic synthesis of C-terminal peptide amides using subtilisin A from Bacillus licheniformis

Boeriu, Carmen G.; Frissen, A.E.; Boer, E.J.M. de; Kekem, Kees van; Zoelen, Dirk-Jan van; Eggen, Ivo F.

doi:10.1016/j.molcatb.2010.03.010

Cited by 19 publications

(13 citation statements)

References 11 publications

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“…Total of 3 methods of peptide synthesis have been developed and improved: Chemical synthesis, which uses chemical reagents to mediate peptide bond formation (Andreu and Rivas 2002), enzymatic synthesis, in which the peptide bond formation is catalyzed by enzymes (Bongers and Heimer 1994; Boeriu and others 2010), and the DNA recombinant technology synthesis, based on the use of cloning and ribosomal techniques from biological systems for peptide formation (Sewald and Jakubke 2002).…”

Section: Peptide Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Bioactive Peptides: Synthesis, Properties, and Applications in the Packaging and Preservation of Food

Espitia¹,

Soares²,

Coimbra³

et al. 2012

Comp Rev Food Sci Food Safe

168

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: Bioactive peptides are protein fragments which have a positive impact on the functions and conditions of living beings. Peptides have shown several useful properties for human health, including antimicrobial, antifungal, antiviral, and antitumor activities. These compounds are produced by almost all species of life. However, they are produced in limited quantities in nature. As a result, researchers have tried to synthesize bioactive peptides to study their properties and applications in various areas. Among their applications in food preservation, peptides have been incorporated into packaging materials. This review begins with a brief description of the methods used for the synthesis, purification, and characterization of peptides. Also, the main bioproperties and mechanisms of action of peptides are discussed. Finally, some applications of peptides are presented, especially their use in active packaging, their effects on the polymeric matrix, and peptide migration.

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Section: Peptide Synthesismentioning

confidence: 99%

“…The formation of a peptide bond by enzyme catalysis can occur through several mechanisms, including the reverse hydrolysis reaction of amides and transpeptidation (Machado and others 2004; Boeriu and others 2010).…”

Section: Peptide Synthesismentioning

confidence: 99%

Bioactive Peptides: Synthesis, Properties, and Applications in the Packaging and Preservation of Food

Espitia¹,

Soares²,

Coimbra³

et al. 2012

Comp Rev Food Sci Food Safe

168

View full text Add to dashboard Cite

show abstract

“…Some researchers [56,57] reported the preparation of nucleosides analogues (antiviral precursors) can be catalyzed by glycosyl transferase (deoxyribosyltranferase). This reaction involves the transfer of a sugar group from a compound (31) to another (32) to form a nucleoside (33) (Scheme-XI). Transaldolase enzyme extracted from E. coli catalyzes the transfer of dihydroxyacetone moiety from one donor substrate (35) to other acceptor substrate (36) (Scheme-XII) [55].…”

Section: Scheme-v: Epoxidation Using Cytochrome P450 Enzymementioning

confidence: 99%

“…Microbial enzymes have various advantages over other plants and animals like microbes can grow in extreme environmental conditions and have short generation time. In general, enzymes act as a machinery of nature to synthesize new organic compounds, already discussed by various researchers [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. This review shows some examples of biocatalysts (enzymes) used for the production of various organic compounds and heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Role of Enzymes in Synthesis of Biologically Important Organic Scaffolds

Gupta

Chundawat

2019

Asian J. Chem.

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Green route of biogenic synthesis of heterocyclic compounds via microbes (bacteria, fungi, virus, yeast, algae, etc.) has the potential to deliver clean manufacturing technology. The application of biocatalysts for the synthesis of novel compounds has attracted increasing attention over the past few years and consequently, high demands have been placed on the identification of new biocatalysts for organic synthesis. Enzymes play an increasingly important role as biocatalysts in the synthesis of key intermediates for the pharmaceutical and chemical industry, and new enzymatic technologies. The characteristics of biocatalyst can be tailored with protein engineering and metabolic engineering methods to meet the desired process conditions. This review discusses the synthetic application of all the six classes of enzymes which are oxidoreductase, transferase, hydrolase, lyase, isomerase and ligase. Enzymes are highly selective catalysts and their contribution to regio-, chemo- and stereoselectivity of compounds were also discussed.

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“…[9] We envisioned that this reaction could be reversed for developing an interconversion reaction of C-terminal peptide a-carboxamides into alkyl esters. Subsequently, these esters can serve as intermediate for further enzymatic peptide elongation, as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

et al. 2011

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Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required and racemisation does not occur rendering purification easier compared to chemical peptide synthesis. In this paper, a novel interconversion reaction of peptide C-terminal a-carboxamides into primary alkyl esters with alcalase was used to develop a fully enzymatic peptide synthesis strategy. For each elongation step a cost-efficient amino acid carboxamide building block was used followed by the interconversion of the elongated peptide carboxamide to the corresponding primary alkyl ester. These peptide esters are the starting materials for the next enzymatic peptide elongation step.

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Optimized enzymatic synthesis of C-terminal peptide amides using subtilisin A from Bacillus licheniformis

Cited by 19 publications

References 11 publications

Bioactive Peptides: Synthesis, Properties, and Applications in the Packaging and Preservation of Food

Bioactive Peptides: Synthesis, Properties, and Applications in the Packaging and Preservation of Food

Role of Enzymes in Synthesis of Biologically Important Organic Scaffolds

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

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