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Synthesis of the Novel Amino Acid 4-Amino-3-(aminomethyl)benzoic Acid (AmAbz) and Its Protected Derivatives as Building Blocks for Pseudopeptide Synthesis

✍ Scribed by Robert Pascal; Régine Sola; Frédéric Labéguère; Patrick Jouin

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 290 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200011)2000:22<3755::aid-ejoc3755>3.0.co;2-i

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✦ Synopsis

4-Amino-3-(aminomethyl)benzoic acid (1) (AmAbz) is a novel unnatural amino acid with promise in applications as a building block for the synthesis of peptidomimetics and as a scaffold for combinatorial chemistry. It was efficiently synthesized in three steps (63% overall yield) from 4-aminobenzoic acid, by means of regioselective amidomethylation with hydroxymethylphthalimide. AmAbz (1) contains three distinct functionalities which could be discriminated from one another. Firstly, Boc 2 O or Fmoc-OSu reacted selectively with the benzylamino group to give the monoprotected derivatives AmAbz(Boc) (8a) or AmAbz(Fmoc) (8b), respectively. The absence of acylation at the arylamino group was also [a]

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