One-pot high-throughput synthesis of β-turn cyclic peptidomimetics-via "volatilizable" supports Article

Li, Y, Yu, Y, Giulianotti, M et al. (2009). One-pot high-throughput synthesis of β-turn cyclic peptidomimetics-via "volatilizable" supports . JOURNAL OF ORGANIC CHEMISTRY, 74(5), 2183-2185. 10.1021/jo802583t

cited authors

  • Li, Y; Yu, Y; Giulianotti, M; Houghten, RA

authors

abstract

  • A promising method for the high-throughput synthesis of linear C-hydroxyalkylamido peptidomimetics and β-turn cyclic peptidomimetics via "volatilizable" aminoalkyl functionalized silica gels is presented. Boc amino acids and carboxylic acids were coupled on functionalized aminoalkyl silica gels using a standard DIC/HOBt coupling protocol. After peptide synthesis, the resin bound peptide was cleaved using a two-step process to obtain the linear C-hydroxyalkylamido peptidomimetics. β-Turn cyclic peptidomimetics were generated by intramolecular S NAT cyclization in an aqueous solution. Both the linear and the cyclic peptidomimetics were obtained with good to excellent yields and purities through a "one-pot" reaction. © 2009 American Chemical Society.

publication date

  • March 6, 2009

published in

Digital Object Identifier (DOI)

start page

  • 2183

end page

  • 2185

volume

  • 74

issue

  • 5