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Volumn 121, Issue 25, 1999, Pages 5919-5929

Versatile functionalization of polylysine: Synthesis, characterization, and use of neoglycoconjugates

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN; CARBOHYDRATE; CHLOROACETAMIDE; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; FUNCTIONAL GROUP; GLYCOCONJUGATE; POLYLYSINE; POLYMER; THIOL DERIVATIVE; WATER;

EID: 0033618074     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984183p     Document Type: Article
Times cited : (74)

References (104)
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    • A variety of uses of neoglycoconjugates has recently been summarized in excellent reviews: (a) Roy, R. Trends Glycosci. Glycotechnol. 1996, 8, 79. (b) Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 413. (c) Kiessling, L. L.; Pohl, N. L. Chem., Biol. 1996, 3, 71. (d) Miyata, T., Nakamae, K. Trends Polym. Sci. 1997, 5, 198.
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    • 3, 40°C, 24 h), followed by treatment with ethanolamine (see ref 12a). We have evidence that such compounds can contain even more carboxylic acid residues (>25%).
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    • note
    • In this paper, poly-L-lysine derivatives are designated as L, poly-D/L-lysine derivatives are designated as D/L, and poly-D-lysine derivatives are designated as D. Polymer identification numbers without an extension do not specify the configuration.
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    • n = 1.2) with chloroacetic acid anhydride in DMF/ 2,6-lutidine gave an impure material. A clean product was obtained when the hydrobromide was transformed into the DMF-soluble tosylate prior to the acylation (for the transformation of polylysine hydrobromide into its tosylate, see ref 23a).
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    • L-8 and all other polymers described are also soluble in DMF and DMSO.
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    • Quantitative carbohydrate incorporation was also achieved when the sodium thiolate of 11 was used, which was prepared from 11 by treatment with 1 equiv of sodium methanolate.
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    • This method has been described earlier in a patent. (a) Thoma, G.; Duthaler, R. O.; Ernst, B.; Magnani, J. L.; Patton, J. T. PCT Int. Appl., WO 97/19105, 1997. A similar procedure has recently been published. (b) Blixt, O.; Norberg, T. J. Carbohydr. Chem. 1997, 16, 143.
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    • note
    • Compound 10 (5:1 α/β-mixture) was obtained from the corresponding tetraacetate by saponification using sodium methanolate in methanol. The reaction mixture was neutralized with Dowex 50Wx8 ion-exchange resin.


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