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Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(1-(3-nitro-dibenzofuran-2-yl)-ethyl)-L-cysteine // Synonyms: Fmoc-Cys(NDBF)-OH, 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-[1-(3-nitro-dibenzofuran-2-yl)-ethylsulfanyl]-propionic acid
|Molecular weight:||582,62 g/mol|
Nitrodibenzofuran is a one- and two-photon sensitive protecting group. Masking the thiol group of cysteine with an NDBF group allows the incorporation of this residue into peptides by standard solid-phase peptide synthesis and selective deprotection by photolysis upon irradiation with UV (365 nm) light or two-photon excitation with near-infrared (800 nm) light. The latter aspect renders this derivative especially useful for biological applications in tissue samples or intact organisms due to increased penetration depth of NIR light as well as lower phototoxicity.
Nitrodibenzofuran: A One- and Two-Photon Sensitive Protecting Group That Is Superior to Brominated Hydroxycoumarin for Thiol Caging in Peptides; M. Mohsen Mahmoodi, D. Abate-Pella, T. J. Pundsack, C. C. Palsuledesai, P. C. Goff, D. A. Blank, and M. D. Distefano; J. Am. Chem. Soc. 2016; 138: 5848-5859. https://doi.org/10.1021/jacs.5b11759
The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells; A. Momotake, N. Lindegger, E. Niggli, R. J. Barsotti, G. C. R. Ellis-Davies; Nat. Methods 2006; 3: 35. https://doi.org/10.1038/nmeth821
Chemical synthesis of a two-photon-activatable chemokine and photon-guided lymphocyte migration in vivo; X. Chen, S. Tang, J.-S. Zheng, R. Zhao, Z.-P. Wang, W. Shao, H.-N. Chang, J.-Y. Cheng, H. Zhao, L. Liu, H. Qi; Nat. Commun. 2015; 6: 7220. https://doi.org/10.1038/ncomms8220
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