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Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

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Abstract

Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J28, isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available d-glucose, l-rhamnose and l-arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl d-glucosamine, d-fucose and d-xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.

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Notes

  1. Preparation of H2SO4–silica: To a slurry of silica gel (10 g, 200–400 mesh) in dry diethyl ether (50 mL) was added commercially available conc. H2SO4 (1 mL) and the slurry shaken for 5 min. The solvent was evaporated under reduced pressure resulting in free flowing H2SO4-silica which was dried at 110°C for 3 h and used for the reactions. For use in various carbohydrate reactions see: Rajput et al. [12]; Rajput and Mukhopadhyay [13]; Mukhopadhyay [14] and Roy and Mukhopadhyay [15].

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Acknowledgment

We thank SAIF (CDRI) for instrumental facility. BR is thankful to CSIR, New Delhi, India for fellowship. The work is funded by DST, New Delhi, India through SERC Fast-Track Grant SR/FTP/CS-110/2005.

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Experimental details and Copies of 1H and 13C spectra of all new compounds.

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Authors and Affiliations

  1. Medicinal and Process Chemistry Division, Central Drug Research Institute, Chattar Manzil Palace, Lucknow, 226 001, Uttar Pradesh, India

    Bimalendu Roy & Balaram Mukhopadhyay

  2. Department of Chemistry, Inorganic Chemistry Section, Jadavpur University, Jadavpur, Kolkata, 700 032, India

    Kausikisankar Pramanik

Authors
  1. Bimalendu Roy
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  2. Kausikisankar Pramanik
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  3. Balaram Mukhopadhyay
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Correspondence to Balaram Mukhopadhyay.

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Central Drug Research Institute (CDRI) Communication No. 7142.

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Roy, B., Pramanik, K. & Mukhopadhyay, B. Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin . Glycoconj J 25, 157–166 (2008). https://doi.org/10.1007/s10719-007-9068-6

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  • DOI: https://doi.org/10.1007/s10719-007-9068-6

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