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AmAz Coupler

AmAz Coupler

CAS No.: 532931-48-9

Synthon that allows for the linking of an amine-containing component to an azide-containing component.
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Our AmAz Coupler allows for the linking of an amine-containing component to an azide-containing component. The amine-containing component is first reacted with the NHS ester and then the azide-containing component is reacted with the phosphine. An intramolecular trapping of the phosphorimidate by the ortho- methyl ester results in a stable aryl-1,4-diamide linkage between the two components.
A modification of the Staudinger azide reduction known as Staudinger ligation provides a way to form an amide bond between an azide containing molecule and an appropriately substituted triaryl phosphine.(1) The Staudinger ligation has been used for fluorescent labeling of DNA by site specific ligation of a 5'-azido oligonucleotide with a preformed fluorescein-ligator conjugate.(2) The utility of this technology in living systems demonstrates the potential for re-engineering a variety of cell and tissue surfaces.(3) Additional applications include site selective post-translational modification of proteins with a biotin-phosphine ligator conjugate,(4) ligation of human recombinant thrombomodulin to liver islets through bifunctional poly(ethylene glycol) (PEG) linkers,(5) and liposome surface functionalization.(6) LKD4260 is therefore a useful intermediate for the preparation of a variety of ligation conjugates.
LKD4260 and the use thereof in chemoselective ligation, is protected by one or more of the following US Patents, the rights of which are assigned to The Regents of the University of California: US 6,570,040, US 7122703, and US 7,838,665. Additional patents are pending. It may be used for research purposes only. It is not licensed for resale and may only be used by the buyer. This product may not be used and is not licensed for clinical assays, where the results of such assays are provided as a diagnostic service. If a diagnostic or therapeutic use is anticipated, then a license must be requested from the University of California. The availability of such diagnostic and therapeutic use license(s) cannot be guaranteed from the University of California.

Ref:

  1. (a) Saxon, E.; Bertozzi, C.R. Science, 2000, 287, 2007-2010. (b) Saxon, E.; Armstrong, J.I.; Bertozzi, C.R. Org. Lett. 2000, 2, 2141-2143.
  2. Wang, C.-Y.; Seo, T.S.; Li, Z.; Ruparel, H.; Ju, J. Bioconjugate Chem. 2003, 14, 697-701.
  3. Prescher, J.A.; Dube, D.H.; Bertozzi, C.R. Nature, 2004, 430, 873-877.
  4. Ohno, S.; Matsui, M.; Yokogawa, T.; Nakamura, M.; Hosoya, T.; Hiramatsu, T.; Suzuki, M.; Hayashi, N.; Nishikawa, K. J. Biochem. 2007, 141, 335-343.
  5. Stabler, C.L.; Sun, X.-L.; Cui, W.; Wilson, J.T.; Haller, C.A.; Chaikof, E.L. Bioconjugate Chem. 2007, 18, 1713-1715.
  6. Zhang, H.; Ma, Y.; Sun, X.-L. Chem. Commun. 2009, 3032-3034.
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