Synthesis of fagopyritols A1 and B1 from d-chiro-inositol

Cid, M. B.; Alfonso, Francisco; Martín‐Lomas, Manuel

doi:10.1016/j.carres.2004.06.021

Cited by 22 publications

(15 citation statements)

References 17 publications

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“…Clinical pharmacological studies show that D-chiro-inositol can help to treat women with polycystic ovarian syndrome by improving insulin sensitivity (Allahbadia et al, 2006;Nestler et al, 2001). These two kinds of inositols are found throughout many living systems, but commonly in legumes and whole grains (Cid et al, 2004). Owing to this, it is necessary to develop an accurate and reliable method to assay two ingredients in black rice bran, their important roles in human health.…”

Section: Introductionmentioning

confidence: 97%

“…Myo-inositol is a fat-solublizing agent that helps to transport fat from the liver (Bennani and Fabre, 2001); be metabolized to phosphatidylinositol, which makes up small, but very significant component of cell membranes (Gibson and Ehrlich, 2008). D-chiro-inositol, another naturally occurring isomer of inositol, acts as secondary messenger in several metabolic processes including blood sugar control (Cid et al, 2004). Clinical pharmacological studies show that D-chiro-inositol can help to treat women with polycystic ovarian syndrome by improving insulin sensitivity (Allahbadia et al, 2006;Nestler et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

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Determination of Myo-inositol and d-chiro-inositol in black rice bran by capillary electrophoresis with electrochemical detection

Kong

Wang

Cao

2008

Journal of Food Composition and Analysis

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Determination of Myo-inositol and d-chiro-inositol in black rice bran by capillary electrophoresis with electrochemical detection

Kong

Wang

Cao

2008

Journal of Food Composition and Analysis

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“…2) pseudodisaccharide 153 ( Fig. 5.37) as the only product in 65 % yield when the reaction temperature was decreased from À40 C to À78 C [67]. In neither case were transbenzoylation processes detected.…”

Section: Superarmed Glycosyl Donors In Glycosylation Reactionsmentioning

confidence: 91%

Armed-Disarmed Concept in the Synthesis of Glycosidic Bond

Miljković

2013

Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry

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-Reid et al. reported [1] that n-pentenyl glycosides undergo chemospecific cleavage 1 ! 2 ! 3, with N-bromosuccinimide under conditions that leave a wide variety of other protecting groups unaffected ( Fig. 5.1).According to the proposed mechanism ( Fig. 5.1), the addition of water to the reaction mixture will lead to hydrolysis but the addition of alcohol or another sugar having a free hydroxyl group will lead to the formation of glycoside or a disaccharide. In the course of these studies, Fraser-Reid et al. [1] observed that sugar molecules having an acyloxy group at the C2 carbon (6 in Fig. 5.2) hydrolyzed much more slowly than if they had an alkoxy group (7 in Fig. 5.2). This observation suggested that the n-pentenyl glycoside could be made more or less reactive (it could be armed or disarmed) by the type of protecting group placed on the C2 oxygen.The ability of the C2 acyloxy group to disarm the n-pentenyl glycoside was rationalized as shown in Fig. 5.3. Thus, it can be assumed that the cyclic halonium ions 8 and 9 are formed reversibly [2] and that the electron density on the glycosidic oxygen is depleted in 2-O-acyl derivatives so that nucleophilic attack of this oxygen on the halonium ion is less favored than in the 2-O-alkyl counterpart 9. The reason for this is that the electron-withdrawing group at the C2 carbon makes the C2 carbon slightly positively charged so that the formation of another positive charge at the C1 carbon is not a favorable process [there cannot exist two positive charges on two neighboring carbons (C1 and C2) (Fig. 5.3).].Consequently, the armed glycosyl donors react with electrophiles faster than the disarmed ones, and therefore in a solution containing both an armed and disarmed glycosyl donor molecules, whereby disarmed glycosyl donor molecules have one free hydroxyl group, the reaction with an electrophile will result in crosscoupling and not self-coupling, i.e., an armed glycosyl donor will react with the disarmed one, whereas a disarmed donor will not react with itself [3] as illustrated in Fig. 5.5. The promoters for the activation of n-pentenyl group [4,5] are iodonium dicollidine perchlorate (IDCP) and N-iodosuccinimide/triethylsilyl triflate (NIS/Et 3 SiOTf).M. Miljkovic, Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry,

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“…[86] Starting from the appropriate penta-O-benzyl-D-chiro-inositol all six isomeric D-galactosaminopyranosyl-D-chiro-inositols have been prepared. [87] …”

Section: Overview Of D-chiro-inositol Derivativesmentioning

confidence: 99%

The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances inmyo‐Inositol Chemistry)

2015

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Cell signalling via inositol phosphates, eg the second messenger myo-inositol 1,4,5-trisphosphate, and phosphoinositides comprises a huge field of biology. Of nine 1,2,3,4,5,6-cyclohexanehexol isomers, myo-inositol is pre-eminent, with "other" inositols (cis-, epi-, allo-, muco-, neo-, L-chiro-, D-chiro-and scyllo-) and derivatives rarer or thought not to exist in nature. However, recently, neoand D-chiro-inositol hexakisphosphates were revealed in both terrestrial and aquatic ecosystems, highlighting the paucity of knowledge of the origins and potential biological functions of such stereoisomers, a prevalent group of environmental organic phosphates, and their parent inositols. Some "other" inositols are medically relevant, e.g. scyllo-inositol (neurodegenerative diseases), and D-chiro-inositol (diabetes). It is timely to consider exploration of roles and applications of "other" isomers and their derivatives, likely by exploiting techniques now well developed for the myo-series.

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Synthesis of fagopyritols A1 and B1 from d-chiro-inositol

Cited by 22 publications

References 17 publications

Determination of Myo-inositol and d-chiro-inositol in black rice bran by capillary electrophoresis with electrochemical detection

Determination of Myo-inositol and d-chiro-inositol in black rice bran by capillary electrophoresis with electrochemical detection

Armed-Disarmed Concept in the Synthesis of Glycosidic Bond

The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances inmyo‐Inositol Chemistry)

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