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Fmoc-L-Ala(BCP)-OH
Nom chimique: N-alpha-(9-Fluorenylmethyloxycarbonyl)-3-(bicyclo[1.1.1]pentan-1-yl)-L-alanine // Synonymes: Fmoc-Ala(BCP)-OH, 3-Bicyclo[1.1.1]pent-1-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
- n° Art.:SCX1240
- n° CAS:2095488-98-3
- Formule:C23H23NO4
- Storage temperature:2-8°C
- Masse moléculaire:377,43 g/mol
from 2 600,00 €
description
Phenol groups bearing drugs suffer rapid first-pass metabolism to glucuronide and sulfate conjugates, resulting in low bioavailability and low plasma concentrations.
An isosteric and biocompatible replacement of phenyl rings is the BCP moiety (bicyclo[1.1.1]pentane). This hypothesis has been successfully demonstrated in the case of Resveratrol: BCP-Resveratrol shows significantly improved half-life in plasma and intrinsic clearance. Metabolite formation, like glucuronide and sulfate conjugation is drastically reduced.
references
Toward Resolving the Resveratrol Conundrum: Synthesis and in Vivo Pharmacokinetic Evaluation of BCP–Resveratrol. Y. L. Goh, Y. T. Cui, V. Pendharkar, and V. A. Adsool; ACS Med. Chem. Lett. 2017; 8: 516-520. https://doi.org/10.1021/acsmedchemlett.7b00018.
A practical metal-free homolytic aromatic alkylation protocol for the synthesis of 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid. N. T. Thirumoorthi, V. A. Adsool; Org. Biomol. Chem. 2016; 14: 9485-9489. https://doi.org/10.1039/c6ob01799a.
Expedient synthesis of 3-phenylbicyclo[1.1.1]pentan-1-amine via metal-free homolytic aromatic alkylation of benzene. N. T. Thirumoorthi, C. J. Shen, V. A. Adsool; Chem. Commun. 2015; 51: 3139-3142. https://doi.org/10.1039/C4CC09655J.
Radical fluorination powered expedient synthesis of 3-fluorobicyclo[1.1.1]pentan-1-amine. Y. L. Goh and V. A. Adsool; Org. Biomol. Chem. 2015; 13: 11597-11601. https://doi.org/10.1039/C5OB02066B.
A New Route to Bicyclo[1.1.1]pentan-1-amine from 1-Azido-3-iodobicyclo[1.1.1]pentane. Y. L. Goh, E. K. W. Tam, P. H. Bernardo, C. B. Cheong, C. W. Johannes, A. D. William, and V. A. Adsool; Org. Lett. 2014; 16: 1884-1887. https://doi.org/10.1021/ol500635p.
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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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