Rink Amide-MBHA Resin

Rink Amide-MBHA resin is less acid sensitive than Rink Amide resin since the benzhydrylamine linker is joined to the support through an electron-withdrawing acetamido spacer. Usually the products are detached from the resin using 95%TFA in DCM and scavengers required by the substrate composition. In addition, Rink Amide-MBHA resin is also useful for peptide syntheses. Previous study has recently reported the syntheses of tri-, tetra- and pentapeptides via a solid phase synthesis methodology by using a Rink Amide MBHA resin[1].
Rink Amide-MBHA resin: 4-(2',4'-Dimethoxypheyl-Fmoc-aminomethyl-phenoxy-acetamido- norleucyl-MBHA resin; Substitution: 0.4 - 0.8 mmole/g resin; Bead size 100- 200 mesh (polystyrene- 1% DVB)
Structure:Appication: Using the Rink Amide MBHA resin and a Fmoc strategy giving C-terminal amide form peptides, substituted benzhydrylamine and benzylamine linkage agents useful for the solid phase peptide synthesis were evaluated for their relative lability toward trifluoroacetic acid. The two most reactive linkage agents studied were compared in the synthesis of two different peptide amides by the N α-9-fluorenylmethyloxycarbonyl protecting group strategy [2].
Reference:
[1] Boussard C, Doyle VE, Mahmood N, Klimkait T, Pritchard M, Gilbert IH. Design, synthesis and evaluation of peptide libraries as potential anti-HIV compounds, via inhibition of gp120/cell membrane interactions, using the gp120/cd4/fab17 crystal structure. Eur J Med Chem. 2002;37(11):883-90.
[2] Michael S. Bernatowicz, Scott B. Daniels, Hubert Köster. A comparison of acid labile linkage agents for the synthesis of peptide C-terminal amides. Tetrahedron Letters Volume 30, Issue 35, 1989, Pages 4645–4648