Cookies on this website
We use cookies to ensure that we give you the best experience on our website. If you click 'Continue' we'll assume that you are happy to receive all cookies and you won't see this message again. Click 'Find out more' for information on how to change your cookie settings.

© 2015 Wiley-VCH Verlag GmbH & Co. KGaA. All rights reserved. Olefin metathesis (OM) is one of the most versatile methods used to create carbon-carbon bonds in molecules. The synthetic strategies that it offers have enabled the construction of biologically active natural products. OM is exploited in various ways in chemical biology. Advances in aqueous metathesis, including the development of water-soluble metathesis catalysts and use of organic co-solvents or surfactants to aid solubility of conventional metathesis catalysts, have laid the groundwork enabling OM on proteins together with earlier work carried out on amino acids and peptides. This chapter describes the laboratory research efforts toward enabling the application of OM to site-selective protein modification. The cross-metathesis (CM) of unsaturated amino acids with allyl alcohol is analyzed. The enhanced reactivity of allyl sulfides (and other allyl chalcogenides) in aqueous metathesis has enabled OM on protein surfaces, and there are increasing numbers of applications in chemical biology and synthetic chemistry.

Original publication

DOI

10.1002/9783527674107.ch17

Type

Chapter

Book title

Handbook of Metathesis: Second Edition

Publication Date

01/01/2015

Volume

2-3

Pages

295 - 309