Molecular and crystal structure of galactinol dihydrate [1-O-(α-d-galactopyranosyl)-myo-inositol dihydrate]

Noguchi, Keiichi; Okuyama, Kenji; Ohno, Shigeru; Hidano, Tetsuhiro; Wakiuchi, N.; Tarui, Tomoko; Tamaki, Hiroyuki; Kishihara, Shiro; Fujii, Susumu

doi:10.1016/s0008-6215(00)00087-2

Cited by 6 publications

(4 citation statements)

References 36 publications

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“…The presence of small amounts of trigalactosyl myo -inositol ( 13 ) and a tetragalactosyl myo -inositol ( 14 ) has been reported (Courtois and Percheron, 1971). The structure of galactinol ( 11 ) has been confirmed (Brown and Serro, 1953; Noguchi et al , 2000). Recently, the structures of digalactosyl myo -inositol ( 12 ) and trigalactosyl myo -inositol ( 13 ) were confirmed by nuclear magnetic resonance (NMR) analysis (W. Gui, B.A.…”

Section: Galactosyl Cyclitols In Legume Seedsmentioning

confidence: 89%

Soluble carbohydrates in legume seeds

Obendorf

Górecki

2012

Seed Sci. Res.

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Mature dry legume seeds may contain up to 30 different soluble carbohydrates. Sucrose is a major component of the total soluble carbohydrates; others include the raffinose family oligosaccharides (RFOs; raffinose, stachyose, verbascose) that are mono-, di- and tri-α-galactosyl derivatives of sucrose. Other galactosides may include α-galactosyl derivatives of the cyclitols myo-inositol (galactinol, digalactosyl myo-inositol and trigalactosyl myo-inositol), d-pinitol (galactopinitol A, digalactosyl pinitol A (ciceritol) and trigalactosyl pinitol A; and galactopinitol B; higher galactosyl oligomers of galactopintiol B have rarely been detected), d-chiro-inositol (fagopyritol B1, fagopyritol B2 and fagopyritol B3) and d-ononitol (galactosyl d-ononitol and digalactosyl d-ononitol). Small amounts of myo-inositol, d-pinitol and d-chiro-inositol may also be present. Raffinose, stachyose and verbascose increase late in seed maturation, with 70% of RFOs accumulating after maximum seed dry weight is attained. RFOs are mostly degraded during germination. Sucrose, myo-inositol, d-pinitol and d-chiro-inositol are synthesized in maternal tissues of some legumes and are transported to and unloaded by seed coats into the apoplastic space surrounding developing seed embryos. Free cyclitols may be 60% of total soluble carbohydrates in leaves and 20% in seed coat cup exudates. Increasing the supply of free cyclitols may increase the accumulation of their respective α-galactosides in mature seeds. Seeds with reduced RFO accumulation, but with normal to elevated concentrations of galactosyl cyclitols (including fagopyritols), have normal field emergence and are also tolerant to imbibitional chilling under laboratory conditions. Molecular structures, biosynthetic pathways, accumulation of soluble carbohydrates in response to seed-expressed mutations and the physiological role of galactosides are reviewed.

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Section: Galactosyl Cyclitols In Legume Seedsmentioning

confidence: 89%

Soluble carbohydrates in legume seeds

Obendorf

Górecki

2012

Seed Sci. Res.

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“…However, in this case, the inositol is attached to the primary alcohol of the ribose. Other sugar–inositol conjugates found in prokaryotic and eukaryotic cells include small molecules such as galactinol ( 25 ), mycothiol ( 26 ) and more complex molecules such as glycosylphosphatidylinositols (GPIs), − acting as anchors for cell-surface proteins. As the inositol moiety is tethered to the anomeric position of the sugar molecule, these compounds can usually be prepared via a straightforward O -glycosylation reaction onto the sugar donor. − The structural feature of an inositol–sugar conjugate with a highly functionalized sec–sec ether linkage as seen in InsAdA is, however, rarely reported in the literature and therefore a unique synthetic route was needed.…”

Section: Resultsmentioning

confidence: 99%

Inositol Adenophostin: Convergent Synthesis of a Potent Agonist of d-myo-Inositol 1,4,5-Trisphosphate Receptors

Döhle

Mills

et al. 2020

ACS Omega

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d-myo-Inositol 1,4,5-trisphosphate receptors (IP3Rs) are Ca2+ channels activated by the intracellular messenger inositol 1,4,5-trisphosphate (IP3, 1). The glyconucleotide adenophostin A (AdA, 2) is a potent agonist of IP3Rs. A recent synthesis of d-chiro-inositol adenophostin (InsAdA, 5) employed suitably protected chiral building blocks and replaced the d-glucose core by d-chiro-inositol. An alternative approach to fully chiral material is now reported using intrinsic sugar chirality to avoid early isomer resolution, involving the coupling of a protected and activated racemic myo-inositol derivative to a d-ribose derivative. Diastereoisomer separation was achieved after trans-isopropylidene group removal and the absolute ribose–inositol conjugate stereochemistry assigned with reference to the earlier synthesis. Optimization of stannylene-mediated regiospecific benzylation was explored using the model 1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol and conditions successfully transferred to one conjugate diastereoisomer with 3:1 selectivity. However, only roughly 1:1 regiospecificity was achieved on the required diastereoisomer. The conjugate regioisomers of benzyl derivatives 39 and 40 were successfully separated and 39 was transformed subsequently to InsAdA after amination, pan-phosphorylation, and deprotection. InsAdA from this synthetic route bound with greater affinity than AdA to IP3R1 and was more potent in releasing Ca2+ from intracellular stores through IP3Rs. It is the most potent full agonist of IP3R1 known and .equipotent with material from the fully chiral synthetic route.

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“…The residue was extracted in water and lyophilized to yield 11.1 mg of 12 (18%), as a 2/1 mixture of diastereoisomers. 1 …”

Section: A-d D-glucopyranosyl-(1!6)-(±)-myo-inositol (1)mentioning

confidence: 99%

“…An aliquot of 9a was quantitatively per-acetylated by the overnight action of a 1/1 (v/v) mixture of Ac 2 O/pyridine 1. H NMR (500 MHz, CDCl 3 ): d 7.40-7.25 (m, 5H · 4, -CH 2 C 6 H 5 ), 5.58 (d, 1H, J = 1.2 Hz, H ortho-OH (50 mL) were stirred for 2 days under an atmosphere of H 2 .…”

mentioning

confidence: 99%