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4-(3-Hydroxy-4-methylpentyl)phenylacetic acid as a new linker for the solid phase synthesis of peptides with Boc chemistry

✍ Scribed by Katri Rosenthal; Mikael Erlandsson; Anders Undén

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 200 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02316-8

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✦ Synopsis

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 Pam linker stable to cleavage of benzylic protective groups with TFMSA/DMS/TFA mixtures. This allows a mild and convenient two step deprotection procedure using the "low TFMSA-high HF". In HF this new linker reacts preferentially in an intramolecular reaction forming a tetrahydronaphthalene derivative.

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