Rink Amide Resin and Rink Amide MBHA Resin

Overview

 

In the late 1980s, applying acid labile linkage agents for the synthesis of C-terminal amides by the Fmoc (N a-9-fluorenylmethyloxycarbonyl) protecting group strategy was studied. A group of scientists from North America evaluated the relative lability of substituted benzhydrylamine and benzylamine linkage agents used for SPPS toward trifluoroacetic acid. Benzhydrylamine and benzylamine are primary alkyl amines and can be used in a number of applications and processes as intermediate and building blocks. They are designed to make attachment to amine supports via a carboxyl  group and cleavage of peptide amide products from support of SPPS under mild acid conditions possible. Rink Amide Resin is the most commonly used SPPS resin in the amide family because it can be easily cleaved by applying TFA treatment. Since the purpose of the synthesis decides which type of resin should be used in the synthesis process,  if a C-terminal amide is required, Rink Amide Resin is normally the natural choice. With benzhydrylamine linker attaching to the solid support via an electron-withdrawing acetamido spacer, it makes Rink Amide MBHA resin be less acid labile than Rink Amide Resin. 

Rink Amide-MBHA Resin is used for Fmoc SPPS of peptide amides. The quickest and most efficient way to synthesise peptides is via standard solid phase peptide synthesis methodology. In order to control the coupling of each amino acid, the backbone amine (position N-terminal) was protected by Fmoc (9-fluorenylmethyloxycarbonyl), which is stable to acidic reagents and tertiary amines but can be readily cleaved under basic conditions. Where necessary, the amino acid side chains were protected by base stable and acid labile groups such as t-Boc (tert-butoxycarbonyl), Pbf (2,2,4,6,7-pentamethyl-dihydrobenzofuran-5-sulfonyl), Trt (trityl) and Pmc (2,2,5,7,8-pentamethyl chroman-6-sulfonyl). Rink Amide MBHA resin was used in the preparation of peptides with C-terminal protected amides to increase stability.

The cleavage, in other words, being able to “deprotect” all side chain protecting groups and detach the peptide from the resin support at the same time, is as important as the synthesis of a protected peptide. In most cases, TFA treatment is used. The cleavage can be performed under mild conditions due to the acid labile characteristic of the rink resins. Generally speaking, amide resins are relatively easier to work with than acid resins because loading the first amino acid can be tricky and risky for acid resins and that’s why scientists prefer to use resins preloaded with the first amino acid or use amide resins in the first place. 

Circling back to Rink Amide MBHA resin, to prepare this resin,  the modified Rink amide linker is attached to MBHA resin in this support via norleucine. Final peptide is cleaved under acid condition from the resin following peptide sequence coupling under neutral conditions. A treatment with 95% TFA can greatly increase the yields and purity from cleavage. 

Solid phase synthesis, which was originally extensively investigated for peptide and other oligomer synthesis, has recently emerged as a powerful method for the construction of libraries of small organic compounds. Many common reactions have been successfully transferred from their solution phase origins to various solid supports.

Comparison between MBHA Resin, Rink Amide Resin and Rink Amide MBHA Resin

MBHA Resin is different from the other two resins but it does have a structure similar to Rink. The names of these resins are quite self-explanatory. Both Rink Amide Resin and Rink Amide-MBHA Resin are Fmoc-protected, while MBHA resin is not. In addition, the cleavage process for MBHA Resin is more chemically difficult than the rink resins. Given that rink resins are considerably more acid labile, the cleaving process can be done with only 1% TFA treatment.

Our line of products

MBHA Resin, Rink Amide Resin and Rink Amide-MBHA Resin are all available at Applied Polytech. We are not just one of the resin wholesale suppliers. Our line of products includes most commonly used solid phase peptide synthesis resin: Wang Resin, Aminomethyl Resin, MBHA Resin, Rink Amide Resin, Rink Amide-AM Resin, Rink Amide-MBHA Resin, 2-Chlorotrityl Chloride Resin, Merrifield Resin, Macroporous Chloromethyl Resin, PAM Resin, Hydroxymethyl Resin, Sieber Resin, preloaded resins and more! You can get those resins cross-linked with 1% of DVB in various loadings and particle sizes. Apart from wholesale resin supplies, Applied Polytech can also offer you a variety of resins in different particle sizes and loadings for lab and research needs. If you are interested in buying, you can place your order online here to purchase those resins at best price!  For more details or any product inquiries, contact us at info@appliedpolytech.com and we are happy to answer any of your questions!