Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling

Kemker I, Schnepel C, Schröder DC, Marion A, Sewald N (2019)
Journal of Medicinal Chemistry 62(16): 7417-7430.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Halogenated L- or D-tryptophan obtained by biocatalytic halogenation was incorporated into RGD peptides together with a variety of alkyl or aryl boronic acids. Suzuki-Miyaura cross-coupling either in solution or on-resin results in side chain-to-tail-cyclized RGD peptides, for example, with biaryl moieties, providing a new dimension of structure-activity relationships. An array of RGD peptides differing in macrocycle size, the presence of D-amino acid, N-methylation, or connectivity between the indole moiety and the boronic acid showed that, in particular, connectivity exhibits a major impact on affinities toward integrins, for example, a(v)beta(3). Structure-activity relationship studies yielded peptides with affinities toward a(v)beta(3) in the low nanomolar range, good selectivity, and high plasma stability. Structural characteristics of representative molecules have been investigated by molecular dynamics simulations, which allowed understanding the observed activity differences.
Erscheinungsjahr
2019
Zeitschriftentitel
Journal of Medicinal Chemistry
Band
62
Ausgabe
16
Seite(n)
7417-7430
ISSN
0022-2623
eISSN
1520-4804
Page URI
https://pub.uni-bielefeld.de/record/2937343

Zitieren

Kemker I, Schnepel C, Schröder DC, Marion A, Sewald N. Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling. Journal of Medicinal Chemistry. 2019;62(16):7417-7430.
Kemker, I., Schnepel, C., Schröder, D. C., Marion, A., & Sewald, N. (2019). Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling. Journal of Medicinal Chemistry, 62(16), 7417-7430. doi:10.1021/acs.jmedchem.9b00360
Kemker, I., Schnepel, C., Schröder, D. C., Marion, A., and Sewald, N. (2019). Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling. Journal of Medicinal Chemistry 62, 7417-7430.
Kemker, I., et al., 2019. Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling. Journal of Medicinal Chemistry, 62(16), p 7417-7430.
I. Kemker, et al., “Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling”, Journal of Medicinal Chemistry, vol. 62, 2019, pp. 7417-7430.
Kemker, I., Schnepel, C., Schröder, D.C., Marion, A., Sewald, N.: Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling. Journal of Medicinal Chemistry. 62, 7417-7430 (2019).
Kemker, Isabell, Schnepel, Christian, Schröder, David C., Marion, Antoine, and Sewald, Norbert. “Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling”. Journal of Medicinal Chemistry 62.16 (2019): 7417-7430.

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