The easy synthesis of 9-hydroxy-9-(4-carboxyphenyl)xanthene l a new linker for the solid phase peptide synthesis of peptide amides is reported. The cleavage conditions were checked and several peptide amides were synthesized using the TentaGel-resin r~ on the Milligen 9050 continuous flow peptide sy
9-Hydroxy-9-(4-carboxyphenyl)fluorene — a new linker for solid phase synthesis
✍ Scribed by Bernd Henkel; Ernst Bayer
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 113 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The convenient synthesis of 9-hydroxy-9-(4-carboxyphenyl)fluorene and its application as a new linker for solid phase synthesis is reported. The loading of the resin-bound linker with carboxytic acids as well as the cleavage conditions were investigated. The release of the carboxylic acids from this system by treatment with acids is hampered due to the electron-withdrawing effect of the carboxamide group in the para position of the phenyl ring of the resin-bound linker.
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The anchoring the first amino acid in Boc chemistry to a 4-(3-hydroxy-4methylpentyl)phenylacetic acid linker is described and compared to the conventional Pam resin. The peptidyl-4-(4-methyl-3-pentoxy)phenylacetamide linkage is slightly more stable to TFA than the Pam linker but in contrast to the P
Treatment of a free amino acid ester with CO 2 followed by exposure to a chlorosilane-containing polystyrene results in its attachment to the solid support. The newly formed silyl carbamate can be employed to build polypeptides at the carboxyl terminus. Cleavage of the (poly)peptide using aqueous HF