Peptide Synthesis Reactions Research Articles

SIDE REACTIONS IN PEPTIDE SYNTHESIS

The base-catalyzed ring closure of beta-benzylaspartyl peptides was efficiently suppressed by the addition of phenols (with electron-withdrawing substituents) to the reaction mixtures. From a series of compounds tested, 2,4-dinitrophenol and pentachlorophenol were the most effective. No direct relationship was found between the acidity of the additives and their ability to suppress the formation of aminosuccinyl peptides. The applicability of 2,4-dinitrophenol and pentachlorophenol in practical syntheses was also examined.

SIDE REACTIONS IN PEPTIDE SYNTHESIS

The base catalyzed ring closure in t-Boc-Asp-X beta-napthylamides was examined in a series of 2-peptide derivatives in which position X was occupied by the neutral and acidic amino acid residues that occur in proteins. Bulkiness and functional groups in the side chain of X have a major effect on the rate of cyclization, e.g. acidic groups slow down the formation of aminosuccinyl derivatives. Rate-enhancing effect can be observed in serine and threonine, while the side reaction is unexpectedly slow when X is methionine.

Side reactions in peptide synthesis. 8. On the phenacyl group in the protection of the .beta.-carboxyl function of aspartyl residues

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSide reactions in peptide synthesis. 8. On the phenacyl group in the protection of the .beta.-carboxyl function of aspartyl residuesMiklos Bodanszky and Jean MartinezCite this: J. Org. Chem. 1978, 43, 15, 3071–3073Publication Date (Print):July 1, 1978Publication History Published online1 May 2002Published inissue 1 July 1978https://doi.org/10.1021/jo00409a035RIGHTS & PERMISSIONSArticle Views112Altmetric-Citations28LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (442 KB) Get e-Alerts Get e-Alerts

Crown ethers as catalysts of fluoride-anion-mediated reactions in peptide synthesis. Part 1. Protection of tryptophan by benzyloxycarbonyl and 2,4-dichlorobenzyloxycarbonyl groups

Protection of the indole ring of tryptophan by benzyloxycarbonyl and 2,4-dichlorobenzyloxycarbonyl groups is described. Unsolvated fluoride anion, generated by the solubilization of potassium fluoride with 18-crown-6, acts as a powerful base which abstracts the proton from the indole nitrogen atom, and the indolide ion can then be acylated with suitable carbonates. No racemization occurs during acylation. The protecting groups can be removed by catalytic hydrogenation or with liquid hydrogen fluoride or hydrazine.

Side reactions in peptide synthesis. 4. Extensive O-acylation by active esters in histidine containing peptides.

Side reactions in peptide synthesis. 4. Extensive O-acylation by active esters in histidine containing peptides.

ChemInform Abstract: SIDE REACTIONS IN PEPTIDE SYNTHESIS. III. INTERMOLECULAR ACYLATION BY AN UNPROTECTED SIDE CHAIN CARBOXYL GROUP

Chemischer InformationsdienstVolume 7, Issue 30 Natural Products ChemInform Abstract: SIDE REACTIONS IN PEPTIDE SYNTHESIS. III. INTERMOLECULAR ACYLATION BY AN UNPROTECTED SIDE CHAIN CARBOXYL GROUP S. NATARAJAN, S. NATARAJANSearch for more papers by this authorM. BODANSZKY, M. BODANSZKYSearch for more papers by this author S. NATARAJAN, S. NATARAJANSearch for more papers by this authorM. BODANSZKY, M. BODANSZKYSearch for more papers by this author First published: July 27, 1976 https://doi.org/10.1002/chin.197630327Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume7, Issue30July 27, 1976 RelatedInformation

Side reactions in peptide synthesis. III. Intermolecular acylation by an unprotected side chain carboxyl group.

Side reactions in peptide synthesis. III. Intermolecular acylation by an unprotected side chain carboxyl group.

A new micro-test for the detection of incomplete coupling reactions in solid-phase peptide synthesis using 2,4,6-trinitrobenzene-sulphonic acid

A rapid micro-test using 2,4,6-trinitrobenzenesulphonic acid has been developed to detect incomplete coupling reactions in solid phase peptide synthesis. This new test will detect 3 nmol of free amino groups per milligram of resin.

ChemInform Abstract: SIDE REACTIONS IN PEPTIDE SYNTHESIS PART 2, FORMATION OF SUCCINIMIDE DERIVATIVES FROM ASPARTYL RESIDUES

Chemischer InformationsdienstVolume 6, Issue 48 Natural Products ChemInform Abstract: SIDE REACTIONS IN PEPTIDE SYNTHESIS PART 2, FORMATION OF SUCCINIMIDE DERIVATIVES FROM ASPARTYL RESIDUES M. BODANSZKY, M. BODANSZKYSearch for more papers by this authorS. NATARAJAN, S. NATARAJANSearch for more papers by this author M. BODANSZKY, M. BODANSZKYSearch for more papers by this authorS. NATARAJAN, S. NATARAJANSearch for more papers by this author First published: December 2, 1975 https://doi.org/10.1002/chin.197548419Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume6, Issue48December 2, 1975 RelatedInformation

Side reactions in peptide synthesis. II. Formation of succinimide derivatives from aspartyl residues.

Side reactions in peptide synthesis. II. Formation of succinimide derivatives from aspartyl residues.

The monitoring of reactions in solid-phase peptide synthesis with picric acid

The monitoring of reactions in solid-phase peptide synthesis with picric acid

A non-destructive method for the determination of completeness of coupling reactions in solid phase peptide synthesis

A non-destructive method for the determination of completeness of coupling reactions in solid phase peptide synthesis