28944-89-0Relevant academic research and scientific papers
Enantioselection in peptide bond formation
Hill, Roger R.,Birch, David,Jeffs, Graham E.,North, Michael
, p. 965 - 972 (2007/10/03)
Selectivity in abiotic condensations of amino acids remains controversial and stereochemically little explored. We find that competitive activated couplings of N-acyl derivatives of glycine, alanine, valine, proline and phenylalanine with binary, ternary and quaternary mixtures of amides and esters of the same group of amino acids show little selectivity among the reactants, except with respect to configuration, where a consistent and significant preference for heterochiral outcomes, mostly >80%, is observed. One possible explanation of this selectivity predicts a predisposition to homochiral coupling under conditions that would require the two carboxyl functions to be co-facial in the activated complex.
Receptor binding mimetics: A novel molecularly imprinted polymer
Kempe, Maria,Mosbach, Klaus
, p. 3563 - 3566 (2007/10/02)
A novel molecularly imprinted polymer was prepared by copolymerization of trimethylolpropane trimethacrylate (1) and methacrylic acid (3) in the presence of a dipeptide acting as the template. The recognition capability of the synthetic receptor-like binding sites produced in the polymer network for the peptide was demonstrated by using the polymer as a chiral stationary phase in HPLC. The polymer was superior to previously reported molecularly imprinted polymers in that unusually high racemic resolution and load capacity were demonstrated.
Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
Funasaki, Noriaki,Hada, Sakae,Neya, Saburo
, p. 1861 - 1867 (2007/10/02)
The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.
