Preparation of bioconjugates through an Ugi reaction

Angewandte Chemie - International Edition

Volumn 39, Issue 12, 2000, Pages 2109-2112

  Ziegler, Thomas ^a   Gerling, Sonja ^a   Lang, Martin ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Bioconjugates; Glycoproteins; Multiple component reactions; Proteins

Indexed keywords

ACETONE; ALDEHYDE DERIVATIVE; AMINE; BIOTIN DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; GLYCOSIDE; ISONITRILE DERIVATIVE; M PROTEIN; RHODAMINE;

ARTICLE; CHEMICAL REACTION; CONCENTRATION RESPONSE; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; PH; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034674257     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000616)39:12<2109::AID-ANIE2109>3.0.CO;2-9     Document Type: Article

References (25)

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16. 2). Compounds 2b and 2c were purchased from Pierce.
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18. [5] by Zemplén saponification (cat. NaOMe in MeOH) and used without further purification. Compound 4d was prepared from N-(3-hydroxypropyl)formamide (L. Goldstein, A. Niv, Appl. Biochem. Biotechnol. 1993, 42, 19-35) with diphosgene according to W. P. Fehlhammer, K. Bartel, B. Weinberger, U. Plaia, Chem. Ber. 1985, 118, 2220-2234.
19. [5] by Zemplén saponification (cat. NaOMe in MeOH) and used without further purification. Compound 4d was prepared from N-(3-hydroxypropyl)formamide (L. Goldstein, A. Niv, Appl. Biochem. Biotechnol. 1993, 42, 19-35) with diphosgene according to W. P. Fehlhammer, K. Bartel, B. Weinberger, U. Plaia, Chem. Ber. 1985, 118, 2220-2234.
20. For the preparation of compound 5a, see: E. Eckhardt, T. Ziegler, Carbohydr. Res. 1994, 264, 253-269. Compound 5b was prepared by hydrogenolysis (Pd/C) from 5-benzyloxycarbonylpentyl-2-acetamido-2-deoxy-β-D-glucopyranoside (T. Ziegler, Carbohydr. Res. 1994, 262, 195-212) and used without any further purification. Compound 5c was purchased from Pierce.
21. For the preparation of compound 5a, see: E. Eckhardt, T. Ziegler, Carbohydr. Res. 1994, 264, 253-269. Compound 5b was prepared by hydrogenolysis (Pd/C) from 5-benzyloxycarbonylpentyl-2-acetamido-2-deoxy-β-D-glucopyranoside (T. Ziegler, Carbohydr. Res. 1994, 262, 195-212) and used without any further purification. Compound 5c was purchased from Pierce.
22. The determination of the epitope density was performed with a Biflex III (Bruker) MALDI-TOF mass spectrometer with sinapinic acid as a matrix and by calibration of the spectrometer with BSA (66 431 Da) and bovine insulin (5734.6 Da). The determination of the average epitope density was done according to the formula: (mass of conjugate - mass of native protein)/(mass of linked remainder).
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