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A New Base‐Labile Anchoring Group for Polymer‐Supported Peptide Synthesis
Author(s) -
Mutter Manfred,
Bellof Dieter
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670739
Subject(s) - chemistry , protecting group , anchoring , hydroxymethyl , piperidine , peptide synthesis , peptide , yield (engineering) , base (topology) , group (periodic table) , stereochemistry , polymer , combinatorial chemistry , polymer chemistry , organic chemistry , biochemistry , mathematical analysis , alkyl , materials science , mathematics , structural engineering , engineering , metallurgy
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.