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2019•Organic LettersRequires access

Protecting-Group-Free Synthesis of Chondroitin 6-Sulfate Disaccharide and Tetrasaccharide

Yong Sheng Chng, Geordi Tristan, George Wai Cheong Yip, Yulin Lam

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Abstract

Chondroitin 6-sulfate (CS-C) is an important glycosaminoglycan that regulates many physiological functions including the development, progression, and metastasis of cancer. To understand its mechanism of action at the molecular level, CS-C molecules of defined length are required. A protecting group-free synthesis of CS-C disaccharide and tetrasaccharide from the CS-A polymer that involves only three steps and furnishes CS-O disaccharide and tetrasaccharide as intermediates is reported.

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What this paper is about

Chondroitin 6-sulfate (CS-C) is an important glycosaminoglycan that regulates many physiological functions including the development, progression, and metastasis of cancer. To understand its mechanism of action at the molecular level, CS-C molecules of defined length are required. A protecting group-free synthesis of CS-C disaccharide and tetrasaccharide from the CS-A polymer that involves only three steps and furnishes CS-O disaccharide and tetrasaccharide as intermediates is reported.

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Available abstract

Chondroitin 6-sulfate (CS-C) is an important glycosaminoglycan that regulates many physiological functions including the development, progression, and metastasis of cancer. To understand its mechanism of action at the molecular level, CS-C molecules of defined length are required. A protecting group-free synthesis of CS-C disaccharide and tetrasaccharide from the CS-A polymer that involves only three steps and furnishes CS-O disaccharide and tetrasaccharide as intermediates is reported.

Key concepts: Tetrasaccharide, Disaccharide, Chemistry, Stereochemistry, Glycosaminoglycan, Chondroitin sulfate, Chondroitin, Protecting group

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