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Fmoc-3-Amino-adamantane-1-carboxylic acid

Chemical name: 3-(9-Fluorenylmethyloxycarbonyl)-amino-adamantane-1-carboxylic acid // Synonyms: (1r,3r)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)adamantane-1-carboxylic acid, 3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)adamantane-1-carboxylic acid

Product code:FAA8505
CAS No.:875211-10-2
Formula:C26H27NO4
Molecular weight:417,51 g/mol
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description

The highly lipophilic, symmetrical adamantly motif is reported for its hydrophobic bulk and spherical shape, proposed by modelling to favor hydrophobic contacts in protein binding pockets. Thus, this non-natural adamantane g-amino acid building block can be used for structure-activity-relationship studies. Furthermore, adamantane is part of various medicinally important compounds.


references

Conjugation to Polymeric Chains of Influenza Drugs Targeting M2 Ion Channels Partially Restores Inhibition of Drug-Resistant Mutants; A. M. Larson, J. Chen, A. M. Klibanov; J. Pharm. Sci. 2013; 102(8): 2450-2459. https://doi.org/10.1002/jps.23644.


Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols; C. E. Müller, D. Zell, R. Hrdina, R. C. Wende, L. Wanka, S. M. M. Schuler, P. R. Schreiner; J. Org. Chem. 2013; 78(17): 8465-8484. https://doi.org/10.1021/jo401195c.


Exploring N-Arylsulfonyl-L-proline Scaffold as a Platform for Potent and Selective anb1 Integrin inhibitors; N. I. Reed, Y.-Z. Tang, J. McIntosh, Y. Wu, K. S. Molnar, A. Civitavecchia, D. Sheppard, W. F. DeGrado, H. Jo; ACS Med. Chem. Lett. 2016; 7(10): 902-907. https://doi.org/10.1021/acsmedchemlett.6b00196.

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