Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
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While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on-resin Suzuki-Miyaura cross-coupling reactions.
García-Pindado , J , Willemse , T , Goss , R , Maes , B U W , Giralt , E , Ballet , S & Teixidó , M 2018 , ' Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides ' , Biopolymers , vol. Early View . https://doi.org/10.1002/bip.23112
© 2018, Wiley Periodicals, Inc. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/bip.23112
DescriptionThis work was supported by MINECO-FEDER (BIO2016–75327-R) and the Generalitat de Catalunya (XRB and 2014-SGR-521). Júlia García was supported by an FPU grant (AP2012–6464). IRB Barcelona is the recipient of a Severo Ochoa Award of Excellence from MINECO. The IWT Flanders and Janssen Pharmaceutica are thanked for providing financial support of T.W. B.U.W.M ad S.B. thank the Research Foundation Flanders (FWO Vlaanderen; Scientific Research Network (WOG)).
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