Synthesis of a Ring-Oxygenated Variant of the 2-Carboxy-6-hydroxyoctahydroindole Core of Aeruginosin 298-A from Glucose

The design and synthesis of a new core structure, a ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole (Choi) from d-glucose, is reported. Choi, a rigid bicyclic unnatural amino acid, is the core structure of about 15 aeruginosins natural compounds. These compounds are thrombin, trypsin,...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-10, Vol.70 (22), p.8687-8692
Main Authors: Nie, Xiaoping, Wang, Guijun
Format: Article
Language:English
Subjects:
Alkylation
Bromides - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Glucose - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemistry
Leucine - analogs & derivatives
Leucine - chemical synthesis
Leucine - chemistry
Magnetic Resonance Spectroscopy
Malonates - chemistry
Methylation
Models, Molecular
Molecular Structure
Oligopeptides - chemistry
Organic chemistry
Oxidation-Reduction
Preparations and properties
Protein Structure, Tertiary
Protons
Substrate Specificity
Thrombin - antagonists & inhibitors
Thrombin - chemistry
Thrombin - metabolism
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Summary:The design and synthesis of a new core structure, a ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole (Choi) from d-glucose, is reported. Choi, a rigid bicyclic unnatural amino acid, is the core structure of about 15 aeruginosins natural compounds. These compounds are thrombin, trypsin, and factor VIIa inhibitors and Choi is important for their biological activity. The ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole can potentially be used as a surrogate of Choi in the design and synthesis of aeruginosin-based thrombin inhibitors.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0507901