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A New Base-Labile Anchoring Group for Polymer-Supported Peptide Synthesis

✍ Scribed by Manfred Mutter; Dieter Bellof

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
461 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new base‐labile anchoring group, derived from 9‐(hydroxymethyl)fluorene‐4‐carboxylic acid (HO~2~CFmoH or HOFmCO~2~H; 7), for polymer‐supported peptide synthesis os described. The synthesis of 7 starting from 2,2′‐biphenyldicarboxylic acid (1) proceeds in an overall yield of 53%. The group HO~2~CFmo exhibits properties similar to the well known Fmoc protecting group: It is stable to acidic conditions and cleavable by 15% piperidine in DMF. In combination with acid labile N^α^‐protecting groups (e.g. Boc, Ddz, Bpoc, Nps etc.), it renders more flexibility to the stepwise synthesis using polymer supports. The versatility of the new anchoring group in solid‐ and liquid‐phase peptide synthesis is demonstrated for the synthesis of a model peptide.

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