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Boc-L-Ala(Adamantyl)-OH
Chemical name: N-alpha-(t-Butyloxycarbonylamino)-1-adamantyl-L-alanine // Synonyms: (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
- Product code:BAA4590
- CAS No.:70874-01-0
- Formula:C18H29NO4
- Molecular weight:323.43 g/mol
Starting at $975.00
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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