Synthesis of Peptide Thioacids at Neutral pH Using Bis(2-sulfanylethyl)amido Peptide Precursors

Pira, Silvain L.; Boll, Emmanuelle; Melnyk, Oleg

doi:10.1021/ol402601j

Cited by 17 publications

(10 citation statements)

References 37 publications

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“…In terms of the preparation of peptide thioacids, the current experiments described here used SPPS. Because several groups have reported the preparation of peptide thioacids from peptide thioester and peptide hydrazide, we can use longer peptide thioacids that can be prepared from peptide thioesters by an Intein system , or chemical thioesterification method − with E. coli expression methods. However, dependent on peptide sequence and length, the combination of DDC with NCL and EPL is more practical for the preparation of the N-terminal long peptide of glycoproteins.…”

Section: Discussionmentioning

confidence: 99%

Glycoprotein Semisynthesis by Chemical Insertion of Glycosyl Asparagine Using a Bifunctional Thioacid-Mediated Strategy

et al. 2021

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Glycosylation is a major modification of secreted and cell surface proteins, and the resultant glycans show considerable heterogeneity in their structures. To understand the biological processes arising from each glycoform, the preparation of homogeneous glycoproteins is essential for extensive biological experiments. To establish a more robust and rapid synthetic route for the synthesis of homogeneous glycoproteins, we studied several key reactions based on amino thioacids. We found that diacyl disulfide coupling (DDC) formed with glycosyl asparagine thioacid and peptide thioacid yielded glycopeptides. This efficient coupling reaction enabled us to develop a new glycoprotein synthesis method, such as the bifunctional thioacid-mediated strategy, which can couple two peptides with the N-and C-termini of glycosyl asparagine thioacid. Previous glycoprotein synthesis methods required valuable glycosyl asparagine in the early stage and subsequent multiple glycoprotein synthesis routes, whereas the developed concept can generate glycoproteins within a few steps from peptide and glycosyl asparagine thioacid. Herein, we report the characterization of the DDC of amino thioacids and the efficient ability of glycosyl asparagine thioacid to be used for robust glycoprotein semisynthesis.

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Section: Discussionmentioning

confidence: 99%

Glycoprotein Semisynthesis by Chemical Insertion of Glycosyl Asparagine Using a Bifunctional Thioacid-Mediated Strategy

et al. 2021

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“…The reaction usually takes place at room temperature to the exception of less reactive alkylazides that require harsher conditions (60 °C, 36 h). Futhermore, this reaction could be extended to the synthesis of acyl-sulfonamides, carbamates, and enamides from the corresponding azido derivatives. ,,− Wong and Fazio further described that the reaction could be accelerated in the presence of a catalytic amount of RuCl 3 , allowing the transformation to proceed at room temperature . The reaction with selenocarboxylates was also described .…”

Section: Amine Surrogatesmentioning

confidence: 99%

Nonclassical Routes for Amide Bond Formation

2016

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The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds. The review aims to comprehensively discuss relevant work, which was mainly done in the field in the last 20 years. Organization of the data follows a subdivision according to substrate classes: catalytic direct formation of amides from carboxylic and amines ( section 2 ); the use of carboxylic acid surrogates ( section 3 ); and the use of amine surrogates ( section 4 ). The ligation strategies (NCL, Staudinger, KAHA, KATs, etc.) that could involve both carboxylic acid and amine surrogates are treated separately in section 5 .

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“…In particular, the Fmoc-SPPS of peptide thioacids is highly challenging, although significant advances have been realized during the past few years. 67,68 In contrast, N -phenylthiocarbonyl peptides are easily prepared using Fmoc-SPPS as discussed before.…”

Section: Synthesis Of Bioconjugates Using Thiocarbamate Chemoselectivmentioning

confidence: 99%

Phenylthiocarbamate orN-Carbothiophenyl Group Chemistry in Peptide Synthesis and Bioconjugation

et al. 2014

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Synthesis of Peptide Thioacids at Neutral pH Using Bis(2-sulfanylethyl)amido Peptide Precursors

Cited by 17 publications

References 37 publications

Glycoprotein Semisynthesis by Chemical Insertion of Glycosyl Asparagine Using a Bifunctional Thioacid-Mediated Strategy

Glycoprotein Semisynthesis by Chemical Insertion of Glycosyl Asparagine Using a Bifunctional Thioacid-Mediated Strategy

Nonclassical Routes for Amide Bond Formation

Phenylthiocarbamate orN-Carbothiophenyl Group Chemistry in Peptide Synthesis and Bioconjugation

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