publication . Article . 2011

Tuning the self-assembly of the bioactive dipeptide L-carnosine by incorporation of a bulky aromatic substituent.

Castelletto, Valeria; Cheng, Ge; Greenland, Barny W.; Hamley, Ian W.; Harris, Peter J. F.;
Open Access
  • Published: 15 Mar 2011 Journal: Langmuir, volume 27, pages 2,980-2,988 (issn: 0743-7463, eissn: 1520-5827, Copyright policy)
  • Publisher: American Chemical Society (ACS)
  • Country: United Kingdom
The dipeptide L-carnosine has a number of important biological properties. Here, we explore the effect of attachment of a bulky hydrophobic aromatic unit, Fmoc\ud [N-(fluorenyl-9-methoxycarbonyl)] on the self-assembly of\ud Fmoc-L-carnosine, i.e., Fmoc-Beta-alanine-histidine (Fmoc-BetaAH). It is shown that Fmoc-BetaAH forms well-defined amyloid fibril containing Beta sheets above a critical aggregation concentration, which is determined from pyrene and ThT fluorescence experiments. Twisted fibrils were imaged by cryogenic transmission electron microscopy. The zinc-binding properties of Fmoc-BetaAH were investigated by FTIR and Raman spectroscopy since the format...
Medical Subject Headings: macromolecular substances
free text keywords: Spectroscopy, Electrochemistry, General Materials Science, Surfaces and Interfaces, Condensed Matter Physics, Carnosine, chemistry.chemical_compound, chemistry, Infrared spectroscopy, Raman spectroscopy, symbols.namesake, symbols, Pyrene, Fibril, Organic chemistry, Dipeptide, Substituent, Self-assembly
Related Organizations
25 references, page 1 of 2

Gariballa, S. E.;Sinclair, A. J. Age and Ageing 2000, 29, 207-210.

Bonfanti, L.;Peretto, P.;De Marchis, S.;Fasolo, A. Prog. Neurobiol. 1999, 59, 333-353.

Hipkiss, A. R.;Michaelis, J.;Syrris, P. FEBS Lett. 1995, 371, 81-85.

Brownson, C.;Hipkiss, A. R. Free Radical Bio. Med. 2000, 28, 1564-1570.

Biochem. Int. 1987, 15, 1105-1113.

Mehta, A. D.;Seidler, N. W. J. Enzym. Inhib. Med. Chem. 2005, 20, 199-203.

Hobart, L. J.;Seibel, I.;Yeargans, G. S.;Seidler, N. W. Life Sci. 2004, 75, 1379- 1389.

McFarland, G. A.;Holliday, R. Exp. Cell Res. 1994, 212, 167-175.

Seidler, N. W.;Yeargans, G. S.;Morgan, T. G. Arch. Biochem. Biophys. 2004, 427, 110-115.

Attanasio, F.;Cataldo, S.;Fisichella, S.;Nicoletti, S.;Nicoletti, V. G.;Pignataro, B.;Savarino, A.;Rizzarelli, E. Biochemistry 2009, 48, 6522-6531.

Brown, C. E.;Antholine, W. E. J. Phys. Chem. 1979, 83, 3314-3319 Thomas, S.;Biswas, N.;Malkar, V. V.;Mukherjee, T.;Kapoor, S. Chem. Phys.

Lett. 2010, 491.

Barrans, Y.;Bellocq, A. M.;Cotrait, M.;Richard, H. J. Mol. Struct. 1976, 30, 225-242.

Zhang, Y.;Gu, H.;Yang, Z.;Xu, B. J. Am. Chem. Soc. 2003, 125, 13680- 13681.

E.;Ulijn, R. V. Adv. Mat. 2006, 18, 611-+ Jayawarna, V.;Richardson, S. M.;Hirst, A. R.;Hodson, N. W.;Saiani, A.;Gough, J. E.;Ulijn, R. V. Acta Biomat. 2009, 5, 934-943 Zhou, M.;Smith, A. M.;Das, A. K.;N.W., H.;Collins, R. F.;Ulijn, R. V.;Gough, J. E. Biomaterials 2009, 30, 2523-2530 Mart, R. J.;Osborne, R. D.;Stevens, M. M.;Ulijn, R. V. Soft Matter 2006, 2, 822-835 Mahler, A.;Reches, M.;Rechter, M.;Cohen, S.;Gazit, E. Adv. Mat. 2006, 18, 1365-+ Adams, D. J.;Butler, M. F.;Frith, W. J.;Kirkland, M.;Mullen, L.;Sanderson, P.

25 references, page 1 of 2
Powered by OpenAIRE Research Graph
Any information missing or wrong?Report an Issue