Dbco c6 acid

Manufactured by Vector Laboratories

Sourced in United States

DBCO C6 acid is a clickable linker molecule used in bioconjugation reactions. It contains a dibenzocyclooctyne (DBCO) group that can undergo strain-promoted alkyne-azide cycloaddition (SPAAC) with azide-modified biomolecules.

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Lab products found in correlation

N n diisopropylethylamine, by Merck Group (2 mentions)

Close spelling variants of this product

DBCO-acid

2 protocols using dbco c6 acid

Synthesis of Eight-Arm PEG-DBCO Macromers

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Eight-arm, 40-kDa PEG-8DBCO macromers were synthesized by coupling DBCO C6 acid (100 mg, 0.3 mmol; Click Chemistry Tools) to PEG-8 amine [0.5 g, 0.025 mmol, weight-average molecular weight (M_w) = 20,000; JenKem USA] using (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (121 mg, 0.32 mmol; ChemPep) as an activator and N,N-diisopropylethylamine as a base (0.175 ml, 1 mmol; Sigma-Aldrich). The reaction was purged with argon and allowed to proceed overnight. The reaction mixture was precipitated in cold diethyl ether (×3) to yield an off-white solid, which was collected by centrifugation, dissolved in water, dialyzed (8-kDa M_W cutoff; Spectrum Chemical) for 48 hours against deionized water, frozen, and lyophilized to yield the final product (93% yield, 80% functionalization by 1H nuclear magnetic resonance).

Yavitt F.M., Kirkpatrick B.E., Blatchley M.R., Speckl K.F., Mohagheghian E., Moldovan R., Wang N., Dempsey P.J, & Anseth K.S. (2023). In situ modulation of intestinal organoid epithelial curvature through photoinduced viscoelasticity directs crypt morphogenesis. Science Advances, 9(3), eadd5668.

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Synthesis of 4-Arm PEG-DBCO Macromer

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Four-arm, 20 kDa PEG-dibenzylcyclooctyne (PEG-4DBCO) macromers were synthesized by coupling DBCO-C6 acid (100mg, 0.3 mmol, Click Chemistry Tools) to 4arm PEG amine (1g, 0.05 mmol, Mw = 20,000, JenKem USA) using (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU, 114mg, 0.3 mmol, ChemPep) as an activator and N,N-diisopropylethylamine as a base (0.139 mL 0.8 mmol, Aldrich). The reaction was allowed to proceed overnight, after which the reaction mixture was precipitated in cold diethyl ether (x3) to yield an off white solid. The product was collected by centrifugation, dissolved in water, dialyzed (8kDa MW cutoff, Spectrum Chemical) for 48 hours against deionized (DI) water, frozen, and lyophilized to yield the final product (90% yield, 85% functionalization by ¹H NMR).

Yavitt F.M., Brown T.E., Hushka E.A., Brown M.E., Gjorevski N., Dempsey P.J., Lutolf M.P, & Anseth K.S. (2020). The effect of thiol structure on allyl sulfide photodegradable hydrogels and their application as a degradable scaffold for organoid passaging. Advanced materials (Deerfield Beach, Fla.), 32(30), e1905366.

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