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Glycoconjugate Journal

, 25:157 | Cite as

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

  • Bimalendu Roy
  • Kausikisankar Pramanik
  • Balaram MukhopadhyayEmail author
Article

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.

Keywords

Saponin Synthesis H2SO4-silica Growth-inhibitory 

Notes

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.

Supporting Information Available

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

Supplementary material

10719_2007_9068_MOESM1_ESM.pdf (8.5 mb)
ESM 1 (PDF 8896 kb)
10719_2007_9068_MOESM2_ESM.pdf (8 mb)
ESM 2 (PDF 8366 kb)

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Bimalendu Roy
    • 1
  • Kausikisankar Pramanik
    • 2
  • Balaram Mukhopadhyay
    • 1
    Email author
  1. 1.Medicinal and Process Chemistry DivisionCentral Drug Research InstituteLucknowIndia
  2. 2.Department of Chemistry, Inorganic Chemistry SectionJadavpur UniversityJadavpurIndia

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