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Gallastegui N.,TU Munich | Stein M.,TU Munich | Schmidt B.,Institute for Organic Chemistry and Biochemistry | Kloetzel P.-M.,Charite Institute For Biochemie | And 4 more authors.
Angewandte Chemie - International Edition | Year: 2011

Lead role: The role of peptidyl α-keto aldehydes as proteasome inhibitors is well established, yet their molecular binding mode requires additional investigation (see picture). A cyclization mechanism that proceeds through hemiketal and Schiff base formation with the nucleophilic N-terminal threonine of β5 is shown to result in the reversible formation of a 5,6-dihydro-2H-1,4-oxazine ring. This agent serves as a new lead for the development of anticancer drugs. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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