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Boc-L-Ala(Adamantyl)-OH
Nom chimique: N-alpha-(t-Butyloxycarbonylamino)-1-adamantyl-L-alanine // Synonymes: (2S)-3-((1s,3R)-adamantan-1-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid, Boc-Ala(Adamantyl)-OH, (S)-Boc-1-adamantyl-alanine, Boc-Ala(Adamantyl)-OH
- n° Art.:BAA4590
- n° CAS:70874-01-0
- Formule:C18H29NO4
- Storage temperature:2-8°C
- Masse moléculaire:323,43 g/mol
from 750,00 €
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 adamantanyl alanine building block can be used for structure-activity-relationship studies. Furthermore, adamantane is part of various medicinally important compounds.
references
Synthesis and Biological Properties of Enkephalin-like Peptides Containing Adamantylalanine in Position 4 and 5; K. Q. Do, R. Schwyzer; Helv. Chim. Acta 1981; 64(7): 2084-2089. https://doi.org/10.1002/hlca.19810640713.
Structure activity of C-terminal modified analogs of Ac-CCK-7; J. W. Tilley, W. Danho, S.-J. Shiuey, I. Kulesha, R. Sarabu, J. Swistok, R. Makofske, G. L. Olson, E. Chiang, V. K. Rusieckt, R. Wagner, J. Michalewsky, J. Triscari, D. Nelson, F. Y. Chiruzzo, S. Weatherford; Int. J. Pept. Res. 1992; 39(4): 322-336. https://doi.org/10.1111/j.1399-3011.1992.tb01592.x.
An Adamantyl Amino Acid Containing Gramicidin S Analogue with Broad Spectrum Antibacterial Activity and Reduced Hemolytic Activity; V. V. Kapoerchan, A. D. Knijnenburg, M. Niamat, E. Spalburg, A. J. de Neeling, P. H. Nibbering, R. H. Mars-Groenendijk, D. Noort, J. M. Otero, A. L. Llamas-Saiz, M. J. van Raaij, G. A. van der Marel, H. S. Overkleeft, M. Overhand; Chem. Eur. J. 2010; 16(40): 12174-12181. https://doi.org/10.1002/chem.201001686.
Tuning hydrophobicity of highly cationic tetradecameric Gramicidin S analogues using adamantane amino acids; A. D. Knijnenburg, V. V. Kapoerchan, E. Spalburg, A. J. de Neeling, R. H. Mars-Groenendijk, D. Noort, G. A. van der Marel, H. S. Overkleeft, M. Overhand; Bioorg. Med. Chem. 2010; 18(23): 8403-8409. https://doi.org/10.1016/j.bmc.2010.09.018.
Structure-Based Design of b5c Selective Inhibitors of Human Constitutive Proteasomes; B.-T. Xin, G. de Bruin, E. M. Huber, A. Besse, B. I. Florea, D. V. Filippov, G. A. van der Marel, A. F. Kisselev, M. van der Stelt, C. Driessen, M. Groll, H. S. Overkleeft; J. Med. Chem. 2016; 59(15): 7177-7187. https://doi.org/10.1021/acs.jmedchem.6b00705.
Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib; G. de Bruin, E. D. Mock, S. Hoogendoorn, A. M. C. H. van den Nieuwendijk, J. Mazurek, G. A. van der Marel, B. I. Florea, H. S. Overkleeft; Chem. Commun. 2016; 52: 4064-4067. https://doi.org/10.1039/C6CC01156J.
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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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