Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides

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Standard

Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides. / Wang, Yuanyuan; Madsen, Anders; Diness, Frederik; Meldal, Morten.

I: Chemistry - A European Journal, Bind 23, Nr. 56, 2017, s. 13869–13874.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Wang, Y, Madsen, A, Diness, F & Meldal, M 2017, 'Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides', Chemistry - A European Journal, bind 23, nr. 56, s. 13869–13874. https://doi.org/10.1002/chem.201702900

APA

Wang, Y., Madsen, A., Diness, F., & Meldal, M. (2017). Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides. Chemistry - A European Journal, 23(56), 13869–13874. https://doi.org/10.1002/chem.201702900

Vancouver

Wang Y, Madsen A, Diness F, Meldal M. Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides. Chemistry - A European Journal. 2017;23(56):13869–13874. https://doi.org/10.1002/chem.201702900

Author

Wang, Yuanyuan ; Madsen, Anders ; Diness, Frederik ; Meldal, Morten. / Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides. I: Chemistry - A European Journal. 2017 ; Bind 23, Nr. 56. s. 13869–13874.

Bibtex

@article{4091c612065c4a9493ac9e42355e5e08,
title = "Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides",
abstract = "Cascade reactions proceeding through peptide-derived N-carbamoyl iminium ions are reported. Two new reactions of N-carbamoyl iminium ions are described, including a stereoselective double cyclization generating N,N′-aminals and an acid-promoted auto-oxidation. Mechanistic investigations revealed that the N,N′-aminal formation is reversible under strongly acidic conditions. Both of these new reactions proved to be completely orthogonal to subsequent CuAAC chemistry. The reactions were performed in solution and on solid support. The robustness and high stereoselectivity of the methodology holds great promise for applications in parallel diversity-oriented synthesis and in combinatorial synthesis for drug screening.",
keywords = "Click chemistry, Conformational analysis, Diversity oriented synthesis, Peptide heterocycles, Pictet-Spengler",
author = "Yuanyuan Wang and Anders Madsen and Frederik Diness and Morten Meldal",
year = "2017",
doi = "10.1002/chem.201702900",
language = "English",
volume = "23",
pages = "13869–13874",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "56",

}

RIS

TY - JOUR

T1 - Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides

AU - Wang, Yuanyuan

AU - Madsen, Anders

AU - Diness, Frederik

AU - Meldal, Morten

PY - 2017

Y1 - 2017

N2 - Cascade reactions proceeding through peptide-derived N-carbamoyl iminium ions are reported. Two new reactions of N-carbamoyl iminium ions are described, including a stereoselective double cyclization generating N,N′-aminals and an acid-promoted auto-oxidation. Mechanistic investigations revealed that the N,N′-aminal formation is reversible under strongly acidic conditions. Both of these new reactions proved to be completely orthogonal to subsequent CuAAC chemistry. The reactions were performed in solution and on solid support. The robustness and high stereoselectivity of the methodology holds great promise for applications in parallel diversity-oriented synthesis and in combinatorial synthesis for drug screening.

AB - Cascade reactions proceeding through peptide-derived N-carbamoyl iminium ions are reported. Two new reactions of N-carbamoyl iminium ions are described, including a stereoselective double cyclization generating N,N′-aminals and an acid-promoted auto-oxidation. Mechanistic investigations revealed that the N,N′-aminal formation is reversible under strongly acidic conditions. Both of these new reactions proved to be completely orthogonal to subsequent CuAAC chemistry. The reactions were performed in solution and on solid support. The robustness and high stereoselectivity of the methodology holds great promise for applications in parallel diversity-oriented synthesis and in combinatorial synthesis for drug screening.

KW - Click chemistry

KW - Conformational analysis

KW - Diversity oriented synthesis

KW - Peptide heterocycles

KW - Pictet-Spengler

U2 - 10.1002/chem.201702900

DO - 10.1002/chem.201702900

M3 - Journal article

C2 - 28833706

AN - SCOPUS:85029307123

VL - 23

SP - 13869

EP - 13874

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 56

ER -

ID: 184355665