Biomimetic peptide

A method based on the DKR of 4-substituted-2-phenyloxazolin-5-one has been apphed to the large-scale synthesis of N-benzoyl-t-t-leucine-butyl ester 19, an important non-natural amino acid intermediate of several biomimetic peptides. The procedure is based on the alcoholysis of 4-t-butyl-2-phenyloxazoUn-5-one 18 with -butanol catalyzed by the lipase from Mucor miehei (Scheme 13.15) [42]. The unreactive enantiomer is racemized in situ by a base-catalyzed reaction. The... 

Ward, P. D. and Brownlee, D. (2000). Rare Earth. New York, NY Springer-Verlag. Wieland, T. (1988). Sulfur in biomimetic peptide syntheses. In The Roots of Modern... 

The era of biomimetic peptide- and sugar-based polymer vesicles has just begun and seems very promising. Bioinspired vesicles are mainly applied for drug deliv-ery/release and the fabrication of composite materials, but could readily be used for biomimetic materials science, biomineralization, and so on. Especially interesting are smart vesicles changing properties in response to an external stimulus (temperature, pH, ions). 

Several systems employ the synthetic polymer poly(ethylene glycol) as the main component which is decorated with biomimetic peptides and/or proteins. PEG-based materials are distinguished by relatively weak non-specific protein adsorption, and thus, can be used to introduce systematically selected cell signalling epitopes to explore their influence on cellular attachment and functions. 

Sanborn, T.J., Messersmith, P.B. and Barron, A.E., 2002. In situ crosslinking of a biomimetic peptide-PEG hydrogel via thermally triggered activation of factor Xlll. 

Th. Wieland, Sulfur in biomimetic peptide synthesis. In Roots of Biochemistry, Fritz Lipmann-Meeting, Berlin 1987 H. Kleinkauf, H.v. Dohren, L. Jaenicke eds. De Gruyter Berlin, New York 1988, p. 213-223. 

See e.g. Th. Wieland, Sulfur in biomimetic peptide syntheses. In Roots of Biochemistry, Fritz Lipmann-Meeting, Berlin 1987. H. Kleinkauf, H.v. Dohren, L. Jaenicke eds., de Gruyter, Berhn 1988, pp 213-223. In this book one finds i.a. reviews on history of biological peptide syntheses W. Gevers, H. Kleinkauf, F. Lipmann, Peptidyl transfers in gramicidin S biosynthesis from enzyme bound thiolester intermediates. Proc. Natl. Acad. Sci. USA 63 1334-1342 (1969)... 

Rezania, A., Healy, K.E. Integrin subunits responsible for adhesion of human osteoblast-Bke cells to biomimetic peptide surfaces. J. Orthop. Res. 17, 615-623 (1999)... 

Rezania, A., and Healy, K. E. (1999), Biomimetic peptide surfaces that regulate adhesion, spreading, cytoskeletal organization, and mineralization of the matrix dqxrsited by osteoblast-like cells, Biotechnol. Prog. 15(1) 19-32. 

ENGINEERING BIOMIMETIC PEPTIDES FOR TARGETED DRUG DELIVERY... 

Mardilovich, A., and E. Kokkoli. 2004. Biomimetic peptide-amphiphiles for functional biomaterials the role of GRGDSP and PHSRN. Biomacromolecules 5(3) 950-957. 

Engineering Biomimetic Peptides for Targeted Drug Delivery Efrosini Kokkoli... 

KrishnamotHthy N, Yacoub MH, Yaliraki SN (2011) A computational modeling approach fOT enhancing self-assembly and biofunctionalisation of collagen biomimetic peptides. Biomataials 32 7275-7285... 

Non-natural Metal Oxide Synthesis Using Biomimetic Peptides... 

While the above systems employ a synthetic polymer as the main component which is decorated with biomimetic peptides a rather different type of biohybrid matrix uses biopolymers as the main component which is further modified in order to exhibit certain desired characteristics. This approach has been elaborated in quite some detail for fibrin, the polymerized form of fibrinogen (see above). For example, an engineered variant form of VEGF that mimics matrix-binding and cell-mediated release by local ceU-associated enzymatic activity was bound to fibrin with the result that the quaUty of angiogenesis in the matrix was substantially improved [123]. 

---