Synthesis of octahydropyrano[3,2- b]pyrrole-2-carboxylic acid derivatives from d-mannose

Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition...

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Bibliographic Details
Published in:Carbohydrate research 2008-07, Vol.343 (10), p.1743-1753
Main Authors: Ella-Menye, Jean-Rene, Nie, Xiaoping, Wang, Guijun
Format: Article
Language:English
Subjects:
Aerguginosin
Bridged Bicyclo Compounds - chemical synthesis
Mannose - chemistry
Octahydroindole 2-carboxylic acid
Pyrans - chemical synthesis
Pyrroles - chemical synthesis
Rigid conformation
Thrombin inhibitor
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Summary:Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2- b]pyrrole 2-carboxylic acids from d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2008.03.017