Synthesis of heparan sulfate tetrasaccharide as a substrate for human heparanase

• Published in: Carbohydrate research Vol. 353; pp. 13 - 21
• Main Authors: Takeda, Naoko, Ikeda-Matsumi, Remina, Ebara-Nagahara, Kaoru, Otaki-Nanjo, Miyuki, Taniguchi-Morita, Kayo, Nanjo, Miwa, Tamura, Jun-ichi
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.05.2012; Elsevier
• Subjects: Biochemistry & Molecular Biology; Carbohydrate Sequence; Chemistry; Chemistry, Applied; Chemistry, Organic; Glucuronidase - metabolism; Glycosaminoglycan; glycosides; Heparan sulfate; Heparanase; Heparitin Sulfate - chemistry; Humans; Life Sciences & Biomedicine; Molecular Sequence Data; Oligosaccharide; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; Oligosaccharides - metabolism; Physical Sciences; Science & Technology; Substrate Specificity; sulfates; Heparan sulfate; Heparanase; Glycosaminoglycan; Oligosaccharide; ASSAY
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2012.03.014

Regiospecifically sulfated heparan sulfate tetrasaccharide, GlcAβ-GlcN(NS6S)α-GlcAβ-GlcN(NS6S)α was first synthesized as an octyl glycoside. Total synthesis was achieved effectively by coupling the corresponding disaccharide units in short steps. [Display omitted] ► Heparan sulfate tetrasaccharides have been synthesized. ► Glycan elongation is available in a stereocontrolled manner. ► Regiospecific N- and O-sulfation of the tetrasaccharide were achieved. ► Unexpected O-sulfation in an aqueous condition was completely suppressed. Regiospecifically sulfated heparan sulfate tetrasaccharide, GlcAβ-GlcN(NS6S)α-GlcAβ-GlcN(NS6S)α was first synthesized as an octyl glycoside. Total synthesis was achieved effectively by coupling the corresponding disaccharide units in short steps.