Acyl azide generation and amide bond formation in continuous-flow for the synthesis of peptides-Reference-Cited by-同舟云学术

Acyl azide generation and amide bond formation in continuous-flow for the synthesis of peptides

Published:2020 Issue:4 Volume:5 Page:645-650
ISSN:2058-9883
Container-title:Reaction Chemistry & Engineering
language:en
Short-container-title:React. Chem. Eng.

Author:

Mata Alejandro¹²³⁴⁵,Weigl Ulrich⁶⁷⁸,Flögel Oliver⁶⁷⁸,Baur Pius⁶⁷⁸,Hone Christopher A.¹²³⁴⁵^ORCID,Kappe C. Oliver¹²³⁴⁵^ORCID

Affiliation:

1. Center for Continuous Flow Synthesis and Processing (CCFLOW)

2. Research Center Pharmaceutical Engineering GmbH (RCPE)

3. 8010 Graz

4. Austria

5. Institute of Chemistry

6. Cilag AG

7. 8200 Schaffhausen

8. Switzerland

Abstract

Acyl azides were safely generated by using nitrous acid in water and reactedin situwithin a flow system. The acyl azide was efficiently extracted into the organic phase containing an amine nucleophile for a highly enantioselective peptide coupling.

Funder

Österreichische Forschungsför-derungsgesellschaft

Bundesministerium für Digitalisierung und Wirtschaftsstandort

Steirische Wirtschaftsför-derungsgesellschaft

Publisher

Royal Society of Chemistry (RSC)

Subject

Fluid Flow and Transfer Processes,Process Chemistry and Technology,Chemical Engineering (miscellaneous),Chemistry (miscellaneous),Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2020/RE/D0RE00034E

Reference51 articles.

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2. Organic Azides: An Exploding Diversity of a Unique Class of Compounds

3. J. Meienhofer , in The Peptides: Analysis, Synthesis, Biology , Academic Press , London, UK , 1979 , ch. 4, vol. 1 , pp. 197–239

4. The Azide Method in Peptide Synthesis: Its Scope and Limitations1

5. Peptide Coupling Reagents, More than a Letter Soup

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