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N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-t-butyloxycarbonyl-N-beta-methyl-L-2,3-diaminopropionic acid

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Formula: C24H28N2O6
CAS: 446847-80-9

Identification

Structural Formula
N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-t-butyloxycarbonyl-N-beta-methyl-L-2,3-diaminopropionic acid
CAS:
446847-80-9
EINECS:
Molecular Formula:
C24H28N2O6
MDL:
Synonym:


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. Reference: 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.


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