Molecular diversity of peptidomimetics: approaches to the solid-phase synthesis of peptidosulfonamides.
In order to use the potential molecular diversity of the peptidosulfonamide peptidomimetics ultimately in libraries, approaches towards the solid-phase synthesis of peptidosulfonamides are a prerequisite. It is shown that peptidosulfonamides can be synthesized by solid-phase synthesis methods using either a Merrifield or a Tentagel resin. Better and more reproducible results are obtained using the latter resin. The possibility to prepare cyclic peptidosulfonamides was illustrated by the synthesis of cyclo-phenylalanyl psi[CH2S(O)2N]-glycine. However, translation of synthesis of peptidosulfonamides in solution to a solid-phase method was rather laborious and still requires careful optimization.
de Bont
D B
DB
Utrecht Institute for Pharmaceutical Sciences, Department of Medicinal Chemistry, Utrecht University, The Netherlands.
Moree
W J
WJ
Liskamp
R M
RM
D000595:Amino Acid Sequence; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001704:Biopolymers / Q000737:chemistry*; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D011137:Polystyrenes / Q000737:chemistry*; D012117:Resins, Synthetic / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
D000890:Anti-Infective Agents; D001704:Biopolymers; C095039:Merrifield resin; D010455:Peptides; D011137:Polystyrenes; D012117:Resins, Synthetic; D013449:Sulfonamides; C101297:Tentagel resin