Pyridoxal 5'-phosphate binding in lysine-modified PAMAM dendrimers: a biomimetic approach

Org Lett. 2009 Aug 20;11(16):3526-9. doi: 10.1021/ol901299e.

Abstract

(G:3-7)-dendri-PAMAM-(APO-Phe-Lys)(x) (2, APO = aminopropanol, Phe = phenylalanine, Lys = lysine) were prepared and used in a binding study with pyridoxal 5'-phosphate. The results revealed a positive dendritic effect, and binding ability was found to vary with the environment. (G:3-7)-dendri-PAMAM-(APO-Phe-Lys)(x) (2) demonstrated better binding ability at higher pH, and protonation of lysine was considered to affect binding. The strongest binding affinity was K(b) = 254.3 mM(-1) at pH 9, which was shown by (G:7)-dendri-PAMAM-(APO-Phe-Lys)(490) (2e).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Dendrimers
  • Hydrogen-Ion Concentration
  • Lysine / chemistry*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Phenylalanine / chemistry
  • Polyamines / chemical synthesis*
  • Polyamines / chemistry
  • Pyridoxal Phosphate / chemistry*
  • Pyridoxal Phosphate / metabolism

Substances

  • Dendrimers
  • PAMAM Starburst
  • Peptides
  • Polyamines
  • Phenylalanine
  • Pyridoxal Phosphate
  • Lysine