Didecyl squarate - A practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis

Glycoconjugate Journal

Volumn 18, Issue 8, 2002, Pages 615-621

  Bergh, Anders ^a   Magnusson, Bengt Göran ^b   Ohlsson, Jörgen ^a   Wellmar, Ulf ^b   Nilsson, Ulf J ^a  

^a LUND UNIVERSITY   (Sweden)

^b Ideon Science Park   (Sweden)

Author keywords

C18 solid phase extraction; Didecyl squarate; Neoglycoconjugates; Squaric decyl ester glycosides

Indexed keywords

ALPHA DEXTRO MANNOPYRANOSE; BETA DEXTRO GLUCOPYRANOSE; DIDECYL SQUARATE; GALABIOSE; GLYCOCONJUGATE; GLYCOSIDE; NEOGLYCOCONJUGATE; REAGENT; SEPHAROSE; SILICON DIOXIDE; SQUARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONJUGATION; CROSS LINKING; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS;

AMINES; CHROMATOGRAPHY, LIQUID; CROSS-LINKING REAGENTS; CYCLOBUTANES; GLYCOCONJUGATES; GLYCOSIDES; GLYCOSYLATION; HORSERADISH PEROXIDASE; N-ACETYLNEURAMINIC ACID; OLIGOSACCHARIDES; PLANT LECTINS; SEPHAROSE; SERUM ALBUMIN, BOVINE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0036702993     PISSN: 02820080     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020639603070     Document Type: Article

References (13)

1. Varki A, Biological roles of oligosaccharides: All of the theories are correct, Glycobiology 3, 97-130 (1993).
2. Dwek RA, Glycobiology: Towards understanding the functions of sugars, Chem Rev 96, 683-720 (1996).
3. Hakomori S-I, Cancer-associated glycosphingolipid antigens: Their structure, organization, and function, Acta Anatomica 161, 79-90 (1998).
4. Wassarman PM, Towards molecular mechanisms for gamete adhesion and fusion during mammalian fertilization, Curr Opin Struct Biol 7, 658-64 (1995).
5. Karlsson K-A, Bacterium-host protein-carbohydrate interactions and pathogenicity, Biochem Soc Trans 27, 471-4 (1999).
6. Magnusson G, Chernyak AY, Kihlberg J, Kononov LO, Synthesis of neoglycoconjugates, In Neoglycoconjugates: Preparation and Application, edited by Lee YC, Lee RT (Academic Press, San Diego, USA, 1994), pp. 53-143.
7. Roy R, The chemistry of neoglycoconjugates, In Carbohydrate Chemistry, edited by Boons G-J (Blackie Academic, London, 1998), pp. 243-321.
8. Tietze LF, Arlt M, Beller M, Glüsenkamp K-H, Jähde E, Rajewsky MF, Squaric acid diethyl ester: A new coupling reagent for the formation of drug biopolymer conjugates. Synthesis of squaric acid ester amides and diamides, Chem Ber 124, 1215-21 (1991).
9. Tietze LF, Schroter C, Gabius S, Brinck U, Goerlach-Graw A, Gabius H-J, Conjugation of p-aminophenyl glycosides with squaric acid diester to a carrier protein and the use of the neoglycoprotein in the histochemical detection of lectins, Bioconjugate Chem 2, 148-53 (1991).
10. Kamath VP, Diedrich P, Hindsgaul O, Use of diethyl squarate for the coupling of oligosaccharide amines to carrier proteins and characterization of the resulting neoglycoproteins by MALDI-TOF mass spectrometry, Glycoconj J 13, 315-9 (1996).
11. Chernyak A, Karavanov A, Ogawa Y, Kovác P, Conjugating oligosaccharides to proteins by squaric acid diester chemistry: Rapid monitoring of the progress of conjugation and recovery of the unused ligand, Carbohydr Res 330, 479-86 (2001).
12. Law KY, Bailey FC, Squaraine chemistry. Synthesis of bis[4-(dimethylamino)phenyl]squarine from dialkyl squarates. Mechanism and scope of synthesis, Can J Chem 64, 2267-73 (1986).
13. Lindhorst TK, Kötter S, Krallmann-Wenzel U, Ehlers S, Trivalent α-D-mannoside clusters as inhibitors of type-1 fimbriae-mediated adhesion of Escherichia coli: Structural variation and biotinylation, J Chem Soc, Perkin Trans 1 823-31 (2001).