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Synthesis of the 6- and 6′-phosphates of 8-methoxycarbonyloctyl 2-O-α-d-mannopyranosyl-α-d-mannopyranoside by Om P. Srivastava; Ole Hindsgaul is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Phosphorylated derivatives of 2-O-a-D-mannopyranosyl-a-D-mannopyranose bearing phosphoric monoesters at OH-6' (l), OH-6 (2), and at both OH-6 and -6' (3) were prepared from &methoxycarbonyloctyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-a-D-mannopyranosyl)-3,4-di-O-benzyl-6-O-(4-methoxyphenyldiphenylmethyl)a-D-mannopyranoside, from which each of the two primary hydroxyl groups was selectively deprotected for subsequent phosphorylation with diphenyl phosphorochloridate . INTRODUCIION D-Mannose 6-phosphate (Man-6-P) is well known as the essential component of a recognition marker involved in the targeting of newly biosynthesized lysosomal enzymes to the lysosomes1-3. Cell surface receptors having a high affinity for Man-6-P have also been demonstrated on fibroblasts4, Chinese hamster ovary cell@, macrophages7, and mouse lymphoma cellsB where they mediate the internalization of phosphorylated glycoconjugatesgJO. The Man-6-P recognition marker in these systems is normally present on "high-mannose", asparagine-linked oligosaccharides which bind to the receptors with affinities far greater than that of the simple Man-6-P monosaccharide (reviewed in ref. ). These observations suggested that the

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Author

Om P. Srivastava; Ole Hindsgaul

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1986

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)