Effects of glycosylation of (2S,4R)-4-hydroxyproline on the conformation, kinetics, and thermodynamics of prolyl amide isomerization
Glycosylation (galactosylation) of (2S,4R)-4-hydroxyproline (Hyp) in the peptide mimic N-acetyl-Hyp-N′-methylamide does not mediate the isomer equilibrium nor the rate of isomerization between the cis- and trans-prolyl amides in water. However, glycosylat
Owens, Neil W.,Braun, Craig,O'Neil, Joe D.,Marat, Kirk,Schweizer, Frank
Selective Enhancement of Proline Raman Signals with Ultraviolet Excitation
Preresonant Raman spectra of Gly-Pro, Pro-Gly, and N-acetylproline methylamide with excitations between 240 and 200 nm are presented.It is shown that, with excitation near 230 nm, vibrations of the X-Pro bond are preferentially enhanced by approximately a factor of 30 relative to vibrations of the normal peptide bond.
Solution structural features of N-acyl homoserine lactones
Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e- withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (-1) contacts between N-acyl O and lactone C′. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues.
Tumminakatti, Shama,Khatri, Bhavesh,Krishnamurti, Vinayak,Athavale, Vishikh,Prabhakaran, Erode N.
supporting information
p. 5771 - 5775
(2015/09/29)
Factors Affecting Conformation in Proline-Containing Peptides
(Equation presented) NMR was used to study the thermodynamics of the cis → trans isomerization for prolyl amide bonds in the compounds shown. The magnitude of Kt/c for C-terminal esters is greater than for the corresponding amides, signifying s
Taylor, Carol M.,Hardre, Renaud,Edwards, Patrick J. B.,Park, Jae H.
p. 4413 - 4416
(2007/10/03)
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