4-(3-Hydroxy-4-methylpentyl)phenylacetic acid as a new linker for the solid phase synthesis of peptides with Boc chemistry
1999 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 40, no 2, 377-380 p.Article in journal (Refereed) Published
The anchoring the first amino acid in Boc chemistry to a 4-(3-hydroxy-4-methylpentyl)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.
Place, publisher, year, edition, pages
1999. Vol. 40, no 2, 377-380 p.
Biochemistry and Molecular Biology
IdentifiersURN: urn:nbn:se:su:diva-25837DOI: 10.1016/S0040-4039(98)02316-8OAI: oai:DiVA.org:su-25837DiVA: diva2:200647