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Synthesis 1994; 1994(1): 28-30
DOI: 10.1055/s-1994-25397
short paper
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Synthesis of N-(2-Acetamido-2-deoxy-β-D-glucopyranosyl) and N-(N,N′-Diacetylchitobiosyl) Amides of L-Histidine

Jakob P. Ley* , Martin G. Peter
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany
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Publication Date:
17 September 2002 (online)

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The synthesis of N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-histidine amide (10) and N-(2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl)-L-histidine amide (11) is achieved via coupling of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylamine (2) and 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3, 6-di-O-acetyl-2-deoxy-β-D-glucopyranosylamine (4), respectively, with N α,N τ-di-Boc-L-histidine (5) in the presence of 2-ethoxy-1-N-ethoxycarbonyl-1,2-dihydroquinoline and subsequent deprotection. Compound 11 is an inhibitor of chitinase from the brine shrimp Artemia salina.