Synthesis of Heparin Oligosaccharides

Lee, Jinq‐Chyi; Lu, Xiangjun; Kulkarni, Suvarn S.; Wen, Yuh‐Sheng; Hung, Shang‐Cheng

doi:10.1021/ja038244h

Cited by 147 publications

(95 citation statements)

References 20 publications

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“…In contrast to literature results, 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO)/NaOCl [21,[49][50][51][52][53][54][55][56] or TEMPO/iodobenzene diacetate [57] oxidation led to a mixture of partially oxidized products, which is probably due to the hydrophobic nature of our fully protected oligosaccharides. [58] A two-step process of Dess-Martin oxidation and subsequent treatment with NaClO 2 [59] also gave inconsistent results.…”

Section: Deprotection Of Shacontrasting

confidence: 99%

Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides

Huang

2006

Chemistry A European J

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Highly efficient syntheses of hyaluronic acid oligosaccharides have been accomplished through the pre-activation based iterative one-pot strategy. A series of oligosaccharides ranging from di-to hexasaccharides were rapidly assembled using only near stoichiometric amounts of the building blocks without aglycon adjustment or purifications of intermediate oligosaccharides. Deprotection and oxidation protocols were developed for protective group removal and oxidation-state adjustment. The availability of such structurally well defined synthetic hyaluronic acid oligosaccharides will greatly facilitate the establishment of detailed structure-function relationships.

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Section: Deprotection Of Shacontrasting

confidence: 99%

Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides

Huang

2006

Chemistry A European J

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“…For example, heparin, heparan sulfate (Jobron & Jacquinet, 1998), dermatan sulfate (Lee et al, 2004).…”

Section: Methodsmentioning

confidence: 99%

“…For background to l-iduronic acids, see : Capila & Linhardt (2002); Jobron & Jacquinet (1998); Lee et al (2004). For the synthesis of iduronic acid derivatives, see: Yu et al (2004); Sanjoy et al (2001); Lubineau et al (2000); Lohman et al (2003).…”

Section: Related Literaturementioning

confidence: 99%

Methyl 2,3-di-O-acetyl-4-O-levulinoyl-1-O-(2,2,2-trichloro-2-iminoethyl)-L-idopyranosiduronate

Cai

Wei

2010

Acta Cryst E

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“…Further, chemical synthesis of non-analog heparin and HS oligosaccharides, larger than hexasaccharides, is extremely difficult, if not impossible, based on currently available methods for carbohydrate synthesis. While a number of groups continue to pursue the synthesis of heparin (48)(49)(50), it is likely that chemical synthesis alone will be incapable of generating most larger oligosaccharide structures. The application of HS biosynthetic enzymes for generating large heparin and HS oligosaccharides with desired biological activities offers a promising alternative approach.…”

Section: Chemoenzymatic Synthesis Of Hs With Biological Activitiesmentioning

confidence: 99%

Anticoagulant heparan sulfate: structural specificity and biosynthesis

Liu

Pedersen

2007

Appl Microbiol Biotechnol

121

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SummaryHeparan sulfate (HS) is present on the surface of endothelial and surrounding tissues in large quantities. It plays important roles in regulating numerous functions of the blood vessel wall, including blood coagulation, inflammation response and cell differentiation. HS is a highly sulfated polysaccharide containing glucosamine and glucuronic/iduronic acid repeating disaccharide units. The unique sulfated saccharide sequences of HS determine its specific functions. Heparin, an analogue of heparan sulfate, is the most commonly used anticoagulant drug. Because of its wide range of biological functions, HS has become an interesting molecule to biochemists, medicinal chemists and developmental biologists. Here, we summarize recent progress towards understanding the interaction between heparan sulfate and blood coagulating factors, the biosynthesis of anticoagulant heparan sulfate and the mechanism of action of heparan sulfate biosynthetic enzymes. Further, knowledge of the biosynthesis of HS facilitates the development of novel enzymatic approaches to synthesize HS from bacterial capsular polysaccharides and to produce polysaccharide end products with high specificity for the biological target. These advancements provide the foundation for the development of polysaccharide-based therapeutic agents.

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Synthesis of Heparin Oligosaccharides

Cited by 147 publications

References 20 publications

Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides

Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides

Methyl 2,3-di-O-acetyl-4-O-levulinoyl-1-O-(2,2,2-trichloro-2-iminoethyl)-L-idopyranosiduronate

Anticoagulant heparan sulfate: structural specificity and biosynthesis

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