Synthesis of 48 Disaccharide Building Blocks for the Assembly of a Heparin and Heparan Sulfate Oligosaccharide Library

Lu, Lung-Dai; Shie, Chi-Rung; Kulkarni, Suvarn S.; Pan, Guan-Rong; Lu, Xiangjun; Hung, Shang‐Cheng

doi:10.1021/ol062464t

Cited by 96 publications

(63 citation statements)

References 29 publications

(13 reference statements)

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“…This preactivation method was also applied for the glycosylation of the acetate analogue 40 (Table 2, entry 6), albeit in a lower yield. Compound 43, which was directly derived from compound 34 in three steps, [17,22] was coupled with compound 27 under the same glycosylation (Table 2, entry 11) in 80 % yield, whereas the use of NIS/TfOH as a promoter afforded the product in 84 % yield ( Table 2, entry 12). Acceptors that contained a linker at the reducing terminus (41, 42, and 44) were also tolerated in the glycosylation reactions to afford their corresponding disaccharides in good yields (Table 2, entries 8, 9, and 13).…”

Section: And4mentioning

confidence: 99%

Expeditious Synthesis of Orthogonally Protected Saccharides through Consecutive Protection/Glycosylation Steps

Liu

et al. 2015

Israel Journal of Chemistry

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We recently developed a facile synthesis to yield orthogonally protected mannose‐ and Gal‐β1,3/4‐GlcNAc‐containing oligosaccharides. With optimized reaction conditions, the protection/glycosylation steps were carried out in a successive manner, without purification of intermediate products. The entire development sequence is herein described in detail, including each installation and removal of protecting groups, the optimization of glycosylation reactions, the successive operation of reaction steps, and further applications for glycan synthesis. We also discuss the unsolved problems and current challenges.

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Section: And4mentioning

confidence: 99%

Expeditious Synthesis of Orthogonally Protected Saccharides through Consecutive Protection/Glycosylation Steps

Liu

et al. 2015

Israel Journal of Chemistry

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“…16 The isolated disaccharide 4 was contaminated by the rearrangement product of trichloroacetimidate donor 2 . The contaminated compound 4 was directly subjected to removal of the benzylidene acetal using trifluoroacetic acid (TFA) in a mixture of CH 2 Cl 2 and water, 17 which made it easy to separate the byproduct to give desired diol 5 . Benzylation of compound 5 with benzyl bromide and NaH in DMF gave the purified benzyl ether 6 in 53% yield over three steps.…”

Section: Resultsmentioning

confidence: 99%

Chemical synthesis of the outer core oligosaccharide of Escherichia coli R3 and immunological evaluation

Shang

Xiao

et al. 2015

Org. Biomol. Chem.

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Lipopolysaccharides (LPS), major virulence determinants in Gram–negative bacteria, are responsible for many pathophysiological responses and can elicit strong immune responses. In order to better understand the role of LPS in host–pathogen interactions and elucidate the immunogenic properties of LPS outer core oligosaccharide, an all α–linked Escherichia coli R3 outer core pentasaccharide was first synthesized with a propyl amino linker at the reducing end. This oligosaccharide was also covalently conjugated to a carrier protein (CRM197) via the reducing end propyl amino linker. An immunological analysis demonstrated that this glycoconjugate can elicit specific anti-pentasaccharide antibodies with in vitro bactericidal activity. These findings will contribute to further exploring this pentasaccharide antigen as a vaccine candidate.

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“…Quite a few bioactive molecules containing a pyranose moiety have been prepared, including the antitumor macrolide Apicularen A (99) [56], the syn-1,3-diol/5,6-dihydropyran-2-one containing cyclooxygenase inhibitors Cryptocaryolone (100), Cryptocaryolone diacetate (101), Cryptocarya triacetate (102) and Tarchonanthuslactone (103) [57], and the sugar moiety of the antifungal Papulacandin C (104) [58] (Fig. 6).…”

Section: Asymmetric Dihydroxylationmentioning

confidence: 99%

Recent Advances in Monosaccharide Synthesis: A Journey into L-Hexose World

D’Alonzo¹,

Guaragna²,

Palumbo

2009

COC

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Last years have witnessed enormous progresses in glycomic field, mainly as a consequence of the crucial role carbohydrates have shown in biological systems. While up to a few years ago attention was mainly focused on the use of easily available D-sugars, a recent interest has emerged around their L-enantiomers, as they have been found to be key components of several bioactive compounds, whether in the form of oligosaccharides, glycopeptides, terpene glycosides or other clinically useful agents. However, L-sugars (L-hexoses especially) are rather rare in nature and not easily accessi-ble from inexpensive sources. As demand for their synthesis in considerable amount and high purity is more and more pressing, intense efforts have been addressed to the development of new and general methodologies for their construction. This review covers the synthetic routes to L-hexoses, mainly those coming from the new century. Methodologies for monosaccharide assembly will comprise de novo approaches, based on carbon chain elongation, hetero Diels-Alder reaction, asymmetric dihydroxylation up to the most recent amino acid-catalyzed aldol addition – as well as D-sugar manipulation strategies, including epimerization by chemical or enzymatic methods. Application of such protocols for the construction of biologically relevant oligosaccharides and natural products will be also briefly mentioned

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Synthesis of 48 Disaccharide Building Blocks for the Assembly of a Heparin and Heparan Sulfate Oligosaccharide Library

Abstract: [Structure: see text] An efficient synthesis of the entire set of suitably protected 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library is described here.

Cited by 96 publications

References 29 publications

Expeditious Synthesis of Orthogonally Protected Saccharides through Consecutive Protection/Glycosylation Steps

Expeditious Synthesis of Orthogonally Protected Saccharides through Consecutive Protection/Glycosylation Steps

Chemical synthesis of the outer core oligosaccharide of Escherichia coli R3 and immunological evaluation

Recent Advances in Monosaccharide Synthesis: A Journey into L-Hexose World

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