Chemistry of Carba-Sugars (Pseudo-Sugars) and their Derivatives

Suami, Tetsuo; Ogawa, Seiichiro

doi:10.1016/s0065-2318(08)60031-1

Cited by 176 publications

(57 citation statements)

References 126 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methyl ether (10) was treated with tetrabutylammonium fluoride to afford alcohol (13) in quantitative yield, which was then oxidized with Dess-Martin periodinane to give b-hydroxyketone (14) quantitatively. Compound 14 was dehydrated with (CF 3 CO) 2 O and pyridine to give an unstable enone (15), which was reduced with NaBH 4 immediately to give allyl alcohol (16) stereoselectively. 11) Compound 16 was deprotected with trifluoroacetic acid in methanol to give 2 in 68% yield.…”

Section: Results and Disscusionmentioning

confidence: 99%

“…After stirring for 1 h, the reaction mixture was treated with saturated aqueous NH 4 Cl, then extracted with CH 2 Cl 2 . The organic layer was dried over MgSO 4 , filtered, and the solvent was removed under reduced pressure to give a crude residue, which was purified with silica gel column chromatography (eluent, 1% MeOH-CH 2 …”

Section: Methyl (1s2r3s4r5r)-5-o-tert-butyldimethylsilyl-34-o-cymentioning

confidence: 99%

“…Cyclohexanoids with multifunctional groups, called carbasugars, [1][2][3][4] have been reported to have various biological activities, such as antifungal, antibacterial, antiviral and anticancer activities. They are thus attractive synthetic targets for chemists.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Usami

Hatsuno

Yamamoto

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

Section: Results and Disscusionmentioning

confidence: 99%

Section: Methyl (1s2r3s4r5r)-5-o-tert-butyldimethylsilyl-34-o-cymentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Usami

Hatsuno

Yamamoto

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Associative interactions between oligosaccharides on glycoproteins and lectins on the surfaces of binding partners can be involved in the initiation steps of many diseases such as influenza, cholera, stomach cancer, and cancer metastasis [3]. An understanding of these initiating binding processes at the molecular level requires the structural determination of oligosaccharides and the quantification of the glycan monosaccharide constituents, which would be essential towards the development of possible cures for many diseases [4,5].…”

mentioning

confidence: 99%

Multiple-reaction monitoring liquid chromatography mass spectrometry for monosaccharide compositional analysis of glycoproteins

Hammad

Saleh

Novotný

et al. 2009

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

A simple, sensitive, and rapid quantitative LC-MS/MS assay was designed for the simultaneous quantification of free and glycoprotein bound monosaccharides using a multiple reaction monitoring (MRM) approach. This study represents the first example of using LC-MS/MS methods to simultaneously quantify all common glycoprotein monosaccharides, including neutral and acidic monosaccharides. Sialic acids and reduced forms of neutral monosaccharides are efficiently separated using a porous graphitized carbon column. Neutral monosaccharide molecules are detected as their alditol acetate anion adducts [M ϩ CH 3 CO 2 ] Ϫ using electrospray ionization in negative ion MRM mode, while sialic acids are detected as deprotonated ions [M Ϫ H] Ϫ . The new method exhibits very high sensitivity to carbohydrates with limits of detection as low as 1 pg for glucose, galactose, and mannose, and below 10 pg for other monosaccharides. The linearity of the described approach spans over three orders of magnitudes (pg to ng). The method effectively quantified monosaccharides originating from as little as 1 g of fetuin, ribonuclease B, peroxidase, and ␣ 1 -acid glycoprotein human (AGP) with results consistent with literature values and with independent CE-LIF measurements. The method is robust, rapid, and highly sensitive. arbohydrates play vital roles in the control of many key biological processes by acting as reciprocating compounds with proteins in molecular recognition events [1,2]. Associative interactions between oligosaccharides on glycoproteins and lectins on the surfaces of binding partners can be involved in the initiation steps of many diseases such as influenza, cholera, stomach cancer, and cancer metastasis [3]. An understanding of these initiating binding processes at the molecular level requires the structural determination of oligosaccharides and the quantification of the glycan monosaccharide constituents, which would be essential towards the development of possible cures for many diseases [4,5].Monosaccharides compositional analysis is commonly performed using gas-chromatography [6 -10], liquid-chromatography [11-13], or capillary electrophoresis [14 -21]. GC/MS chromatography with an electron-impact ion source has been the traditional method of choice for the quantification of neutral monosaccharides. GC analysis of the trimethylsilyl ether derivatives of sugars is a well-known procedure [9], as is the GC separation of sugars as alditol acetates [7]. However, sample preparation for GC is extensive, involving the derivatization of sugars with specialty reagents to render them more volatile [10]. Also, the sensitive chromatographic operating parameters for GC are not well suited for routine analysis. Liquid chromatography analysis of monosaccharides is complicated by the fact that these compounds do not possess a UV chromophore and consequently, laborious derivatization with chromophores or fluorophores is required before UV or fluorescence detection [22][23][24][25][26]. Neutral sugars have also been analyzed by HPLC using...

show abstract

“…Several antibiotics and compounds of biological interest incorporate glycosides of pseudosugars [1][2][3] or carba-sugars 4 , since, they are endowed with relatively greater stability towards glycosidase-induced hydrolysis. Besides the application as enzyme inhibitors, the carba-sugars are discussed as synthetic intermediates for the preparation of more efficient drugs in order to substitute carbohydrate moieties 5 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pseudo saccharide precursors through ‘off template site’ Michael –Wittig reaction on sugar derived enal

Sharma¹,

Chander²,

Krishna³

et al. 2004

Arkivoc

View full text Add to dashboard Cite

Abstract[3+3] Annulation protocol at an'off template site' on the sugar derived enal synthon effectively resulted in the formation of C-C linked pseudo saccharide precursors. Thus, the enolate of phosphorane generated from ethyl acetoacetate first undergoes a Michael reaction on the enal followed by a Wittig reaction to furnish the target saccharides, where the chirality is very effectively translated from the parent sugar.

show abstract

Chemistry of Carba-Sugars (Pseudo-Sugars) and their Derivatives

Cited by 176 publications

References 126 publications

Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Synthesis of the Epimer of Pericosine B from (-)-Quinic Acid

Multiple-reaction monitoring liquid chromatography mass spectrometry for monosaccharide compositional analysis of glycoproteins

Synthesis of pseudo saccharide precursors through ‘off template site’ Michael –Wittig reaction on sugar derived enal

Contact Info

Product

Resources

About