N-hydroxysuccinimide carbonates and carbamates are useful reactive reagents for coupling ligands to lysines on proteins

Journal of Biochemical and Biophysical Methods

Volumn 38, Issue 1, 1999, Pages 17-28

  Morpurgo, Margherita ^a   Bayer, Edward A ^a   Wilchek, Meir ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Activated N hydroxysuccinimidyl carbamates; Functional group specific modification of primary amines; Ligand coupling

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; LYSINE; PROTEIN; REAGENT; SUCCINIMIDE DERIVATIVE;

ARTICLE; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN MODIFICATION;

AVIDIN; BIOTIN; CARBAMATES; CARBONATES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME-LINKED IMMUNOSORBENT ASSAY; ESTERS; HYDROLYSIS; IMMUNOGLOBULIN G; LECTINS; LIGANDS; LYSINE; PROTEIN BINDING; SUCCINIMIDES;

EID: 0033012003     PISSN: 0165022X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0165-022X(98)00027-X     Document Type: Article

References (20)

1. Lundblad R, Bradshaw R. Application of site-specific chemical modification in the manufacture of biopharmaceuticals: I. an overview. Biotechnol Appl Biochem 1997;26:143-51.
2. Haughland RP. Molecular probes. In: Handbook of fluorescent probes and research chemicals, sixth edition. OR: Eugene. 1997:679.
3. Hermanson G. Bioconjugate techniques. San Diego: Academic Press, 1996:785.
4. Ogura H, Kobayashi T, Shimizu K, Kawabe K, Takeda K. A novel active ester synthesis reagent (N,N′-disuccinimido carbonate). Tetrahedron Lett 1979;49:4745-6.
5. Takeda K, Agaki Y, Saiki A, Tsukahara T, Ogura H. Convenient methods for syntheses of active carbamates, ureas and nitrosoureas using N,N′-disuccinimido carbonate (DSC). Tetrahedron Lett 1983;24:4569-72.
6. Kokubo T, Sassa S, Kaiser E. Flavohemoglobin: A semisynthetic hydrolase acting in the absence of reductase. J Am Chem Soc 1987;109:606-7.
7. Gosh AT, Duong TT, McKee SP, Thompson WJ. N,N′-succinimidyl carbonate: A useful reagent for alkoxycarbonylation of amines. Tetrahedron Lett 1992;3:2781-4.
8. Wilchek M, Miron T. Activation of Sepharose with N,N′-disuccinimidyl carbonate. AppI Biochem Biotechnol 1985;11:191-3.
9. Miron T, Wilchek M. A simplified method for the preparation of succinimidyl carbonate polyethylene glycol for coupling to proteins. Bioconjugate Chem 1993;4:588-9.
10. Wilchek M, Bayer EA. Avidin-biotin Technology. In: Methods in enzymology, Vol. 184. San Diego: Academic Press 1990;184:746.
11. Jacoby W, Wilchek M. Affinity labeling. In: Methods in enzymology, Vol. 46. San Diego: Academic Press, 1977:479-92, 501-4, 508-16.
12. Tchernychev B, Rabinkov A, Mirelman D, Wilchek M. Natural antibodies to dietary proteins: the existence of natural antibodies to alliinase (Alliin lyase) and mannosespecific lectin from garlic (Allium sativum) in human serum. Immunol Lett 1995;47:53-7.
13. Sutoh K, Yamamoto K, Wabayashi T. Electron microscope visualization of the SH thiol of myosin by the use of an avidin biotin system. J Mol Biol 1984;178:323-39.
14. Habeeb AFSA. Determination of free amino groups in protein by trinitrobenzensulfonic acid. Anal Biochem 1966;14:328-36.
15. Miron T, Wilchek M. Immobilization of proteins and ligands using chlorocarbonates. Methods Enzymol 1987;135:84-90.
16. Green NM. A spectrophotometric assay for avidin and biotin based on binding of dyes by avidin. Biochemical J 1965;94:23c-4c.
17. Green NM. Spectrophotometric determination of avidin and biotin. Methods Enzymol 1970;18:418-24.
18. Becker J, Wilchek M, Katchalsky E. Irreversible inhibition of biotin transport in yeast by biotinyl-p-nitrophenyl ester. Proc Natl Acad Sci USA 1971;68:2604-7.
19. Cuatrecasas P, Wilchek M, Anfinsen C. Selective enzyme purification by affinity chromatography. Proc Natl Acad Sci USA 1968;61:636-43.
20. Wilchek M, Miron T. Limitations of N-hydroxysuccinimide esters in affinity chromatography and protein immobilization. Biochemistry 1987;26:2155-61.