By Miklos Bodanszky, John Bendall
Research of peptides and backbone in their fundamental constitution. Conformational research: secondary-tertiary constitution. Peptide synthesis: security, activation and coupling, undesired reactions and their prevention, layout of man-made schemes.
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Chern. : Acta Chern. Scand. : Eur. J. Biochern. : Biochern. Biophys. , Zarnboni, M. in Methods in Enzymology, Vol. 91 (Hirs, C. W. H. and TirnashefT, S. N. 311 Gray, W. , Hartley, B. : Biochern. J. : J. BioI. Chern. , Jorpes, J. : Eur. J. Biochern. : Biochern. J. 39, 507 (1945) Additional Sources Greenstein, J. P. , Sequential Analysis of Peptides in Chemistry of the Amino Acids, p. 1512. New York, J. Wiley and Sons 1961 Gray, W. , Dansyl Chloride Procedure in Methods of Enzymology, Vol. 11 (Hirs, C.
In more recent times also reverse turns (hairpin turns, y-turns) were postulated (Venkatachalam 1968) and then recognized as frequent contributors to peptide and protein conformation. The a-helix is a spiral structure stabilized by intramolecular hydrogen bonds between carbonyl oxygens and amide nitro gens four residues apart: C II o H I N Architectural Features in Peptides 41 The hydrogen bonds are parallel to the axis of the helix and close a ring of 14 atoms including the hydrogen. 4 A. 5 A spacing was observed in x-ray diffraction patterns of powders of certain helical polyamino-acids and also of proteins of high helix content.
The confusion generated by such undesired fragmentation can be reduced by several methods, for instance by permethylation. The acetyl peptide methyl ester is treated with sodium hydride and then with methyl iodide CH3CO-NH-CHR-CO-NH-CHR'-CO-NH-CHR"-CO-OCH3~ 2. CH 3 l CH 3 CH 3 CH 3 CH3CO- ~ -CHR-CO- ~ -CHR' -CO- ~ -CHR" -CO-OCH3 Sequence Determination with the Help of Mass Spectra 27 in order to further reduce polarity of the molecule and to increase its thermal stability. Of course, alkylation extends to other nitrogen atoms as well and the imidazole nucleus of histidine and the indole in tryptophan are also alkylated.
Peptide Chemistry: A Practical Textbook by Miklos Bodanszky, John Bendall