Peptide Fragment Coupling Using a Continuous-Flow Photochemical Rearrangement of Nitrones

Go with the flow: A general approach for amide bond formation by way of a continuous‐flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl‐alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetr...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 15; pp. 4251 - 4255
Main Authors Zhang, Yuan, Blackman, Melissa L., Leduc, Andrew B., Jamison, Timothy F.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.04.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amides
Bonding
Chemistry
Chemistry, Multidisciplinary
Construction
continuous flow
Fragmentation
Joining
Molecular Structure
Nitrogen Oxides - chemistry
nitrones
Peptide Fragments - chemistry
Peptides
Photochemical
Photochemical Processes
photochemistry
Physical Sciences
Science & Technology
continuous flow
IRRADIATION
amides
OXAZIRIDINES
photochemistry
OXAZIRANES
LIGHT
peptides
nitrones
ALDEHYDES
DERIVATIVES
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Summary:Go with the flow: A general approach for amide bond formation by way of a continuous‐flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl‐alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling.
Bibliography:istex:5B0A33DEB19C883A162698ACF26E74AE85792B44
Novartis-MIT Center for Continuous Manufacturing
ark:/67375/WNG-PJKWFCGD-C
ArticleID:ANIE201300504
We are grateful to the Novartis-MIT Center for Continuous Manufacturing for financial support. We thank several colleagues at MIT (Dr. Andrew S. Kleinke, Dr. James J. Mousseau, Dr. Ping Zhang, and Kurt Armbrust) and at Novartis (Dr. Guido Koch, Dr. Berthold Schenkel, Dr. Gerhard Penn, Dr. Benjamin Martin, and Dr. Jörg Sedelmeier) for insightful discussions. We also thank Eric Standley (MIT) and Li Li (MIT) for obtaining mass spectrometric data.
We are grateful to the Novartis‐MIT Center for Continuous Manufacturing for financial support. We thank several colleagues at MIT (Dr. Andrew S. Kleinke, Dr. James J. Mousseau, Dr. Ping Zhang, and Kurt Armbrust) and at Novartis (Dr. Guido Koch, Dr. Berthold Schenkel, Dr. Gerhard Penn, Dr. Benjamin Martin, and Dr. Jörg Sedelmeier) for insightful discussions. We also thank Eric Standley (MIT) and Li Li (MIT) for obtaining mass spectrometric data.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201300504