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Fmoc-L-Dap(Boc,Me)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-t-butyloxycarbonyl-N-beta-methyl-L-2,3-diaminopropionic acid // Synonyms: Fmoc-Dap(Boc,Me)-OH, Fmoc-Dap(Me)(Boc)-OH, N-alpha-Fmoc-N-beta-Boc-N-beta-methyl-L-2,3-diaminopropionic acid,(S)-3-{[(t-butyloxy)carbony](methyl)amino}-2-{[(9H-fluoren-9-ylmethyloxy)carbonyl]amino}p ropanoic acid
- Product code:FAA4195
- CAS No.:446847-80-9
- Formula:C24H28N2O6
- Storage temperature:2-8°C
- Molecular weight:440,49 g/mol
- Purity :min. 99%
- Enantiomeric Purity:min. 99,7%
from €144.00
description
This building block has been used to show how Coulombic interactions between ionizable 2,3-diaminopropionic acid (Dap) side chains can be manipulated to tune the functional pH response of a peptide. This will lead to alter nucleic acid transfer and hydrogen bonding capabilities, resulting in reduced cytotoxicity.
Fmoc-Dap(Boc,Me) is used in basic amino acid containing peptide synthesis.
references
Manipulating the pH response of 2,3-diaminopropionic acid rich peptides to mediate highly effective gene silencing with low-toxicity; Vincenzo Abbate,Wanling Liang, Jayneil Patel, Yun Lan, Luigi Capriotti, Valentina Iacobucci, Tam T. Bui, Poulami Chaudhuri, Laila Kudsiova, Louic S. Vermeer, Patrick F.L. Chan, Xiaole Kong, Alex F. Drake, Jenny K.W. Lam, Sukhvinder S. Bansal, and A. James Masona; J Control Release 2013; 172(3): 929-938. doi: 10.1016/j.jconrel.2013.09.033.
Z.P. Huang, j.T. Du, X.Y. Su, Y.X. Chen, Y.F. Zhao, Y.M. Li; Amino Acids 2007; 33: 85-89.
R. Wienecke, A. Bernecker, R. Riedel, M. Sumper, C. Steinem, A. Geyer; Org. Biomol. Chem. 2011; 9: 5482-5486.
Z.-P. Huang, J.-T. Du, Y.F. Zhao, Y.-M. Li; Int. J. Pept. Res. Ther. 2006; 12: 187-193.
J. Chatterjee, B. Laufer, H. Kessler; Nat. Protoc. 2012; 7: 432-444.
R.J. Hopkinson, R.B. Hamed, N.R. Rose, T.D.W. Claridge, C.J. Schofield; ChemBioChem 2010; 11: 506-510.
L. Monfregola, S. De Luca; Amino Acids 2011; 41: 981-990.
L. Monfregola, M. Leone, E. Calce, S. De Luca; Org. Lett. 2012; 14: 1664-1667.
Kretsinger, Juliana K.; Schneider, Joel P. Journal of the American Chemical Society (2003), 125(26), 7907-7913. DOI:10.1021/ja029892o;
Obrecht, Daniel; Luther, Anatol; Bernardini, Francesca; Zbinden, Peter; Lederer, Alexander PCT Int. Appl. (2016), WO 2016150576 A1.
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