Association of model peptides and dehydropeptides: N-acetyl-L-butyrine and [Z]-dehydrobutyrine N',N'-dimethylamides

• Autorzy: Broda M. A. , Rzeszotarska B.
• Języki publikacji: EN

Abstrakty

EN

These comparative studies on the aggregation behaviour of Ac-(Z)-ΔAbu-NMe2 and Ac-L-Abu-NMe2 in carbon tetrachloride were performed by the analysis of their FTIR spectra and by theoretical calculations. The percentage of the monomeric form (α) decreased as concentration increased and this occurred to a higher degree for the (Z)-ΔAbu derivative than for its saturated analogue. The dimerization constant KD, calculated on the basis of the intensity of the monomer and associate bands in the νs(N-H) vibration region, is by three orders of magnitude larger for Ac-(Z)-ΔAbu-NMe2 than for Ac-L-Abu-NMe2. The obtained dimer geometries of the dehydro- compound were calculated by the B3LYP/6-31+G** method.

Słowa kluczowe

EN

N-acetyl-L-butyrine; peptide; bioactive peptide; beta-dehydroamino acid; alpha-dehydroamino acid; [Z]-dehydrobutyrine N',N'-dimethylamide; dehydropeptide

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2006
• Tom: 53
• Numer: 1
• Opis fizyczny: p.221-226,fig.,ref.

Twórcy

autor

Broda M. A.

• University of Opole, Opole, Poland

autor

Rzeszotarska B.

Bibliografia

• Boys BS, Bernardi F (1970) Mol Phys 19: 553–556.
• Broda MA, Rospenk M, Siodłak D, Rzeszotarska B (2005a) J Mol Struct 740: 17–24.
• Broda MA, Siodłak D, Rzeszotarska B (2005b) J Peptide Sci 11: 546–555.
• Broda MA, Siodłak D, Rzeszotarska B (2005c) J Peptide Sci 11: 235–244.
• El-Masdouri L, Aubry A, Boussard G, Marraud M (1992) J Peptide Protein Res 40: 482–486.
• Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T Jr, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision B.04, Gaussian, Inc., Pittsburgh PA.
• GRAMS/386 Version 3.01B. Galactic Industries Corp., Salem NH, 1994.
• Hruby VJ, Li G, Haskell-Luevano C, Shenderowich M (1997) Biopolymers (Peptide Sci) 43: 219–266.
• Hruby VJ, Balse PM (2000) Curr Med Chem 7: 945–970.
• Hruby VJ (2001) Acc Chem Res 34: 389–397.
• Mizuno K, Nishio S, Shindo Y (1979) Biopolymers 18: 683–708.
• Rzeszotarska B, Siodłak D, Broda MA, Dybała I, Kozioł AE (2002) J Peptide Res 59: 79–89.
• Siodłak D, Broda MA, Rzeszotarska B, Dybała I, Kozioł AE (2003) J Peptide Sci 9: 64–74.
• Siodłak D, Broda MA, Rzeszotarska B (2004a) J Mol Struct (Theochem) 668: 75–85.
• Siodłak D, Rzeszotarska B, Broda MA, Kozioł AE, Kołodziejczyk E (2004b) Acta Biochim Polon 51: 145–152.
• Siodłak D, Broda MA, Rzeszotarska B, Kołodziejczyk E, Kozioł AE (2004c) Z Kristallogr 219: 231–238.
• Steiner T (2002) Angew Chem Int Ed Engl 41: 48–76.
• Zimmerman SS, Pottle MS, Némethy G, Scheraga HA (1977) Macromolecules 10: 1–9.