57029-86-4Relevant academic research and scientific papers
Total Synthesis of Phospholipomannan of Candida albicans
Ali, Asif,Gannedi, Veeranjaneyulu,Singh, Parvinder Pal,Vishwakarma, Ram A.
, p. 7757 - 7771 (2020/07/25)
First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.
Efficient regioselective protection of myo-inositol via facile protecting group migration
Nkambule, Comfort M.,Kwezi, Nomfundo W.,Kinfe, Henok H.,Nokwequ, Mbulelo G.,Gammon, David W.,Oscarson, Stefan,Karlsson, Erik
, p. 618 - 623 (2011/03/19)
A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.
COMPOUNDS AND COMPOSITIONS FOR THE DETECTION AND TREATMENT OF ALZHEIMER'S DISEASE AND RELATED DISORDERS
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, (2009/10/22)
One aspect of the present invention relates to compounds, compositions and methods for diagnosis and/or treatment of a subject suffering from an amyloidosis-associated pathological condition. In certain embodiments, the imaging and/or therapeutic agents of the instant invention may be administered to a subject for identification and/or treatment of amyloid deposits. A specific imaging method detects amyloid deposits by administering the imaging agent to the subject and detecting the spatial distribution of the agent. Differential accumulation of the agent is indicative of AD or an amyIoidosis-associated pathological condition and can be monitored by using a PET or SPECT camera.
Total synthesis of spicamycin
Suzuki, Tamotsu,Suzuki, Sayaka T.,Yamada, Iwao,Koashi, Yoshiaki,Yamada, Kazue,Chida, Noritaka
, p. 2874 - 2880 (2007/10/03)
The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.
Syntheses of novel hybrid vitamin C derivatives: Stability and biological activity
Morisaki, Kazuo,Ozaki, Shoichiro
, p. 725 - 734 (2007/10/03)
A novel series of hybrid L-ascorbic acid (vitamin C) derivatives linking other biologically active substances glycolic acid, myo-inositol, and α-tocopherol (vitamin E) at the C-2 or C-3 hydroxyl group were synthesized, and their thermal stability and inhibitory activities against tyrosinase-catalyzed melanin formation, active oxygen species (AOS), and free radicals were evaluated in vitro. Among these derivatives, 2-O-carboxymethylascorbic acid had high thermal stability as well as moderate inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals compared to other typical inhibitors and scavengers. On the other hand, 3-O-carboxymethylascorbic acid was markedly unstable in aqueous solution. The 2-O-carbonylmethyl derivatives linking myo-inositol or vitamin E were susceptible to degrading, however the vitamin E derivative had stronger inhibitory activities against AOS and free radicals than free vitamin C.
Synthesis of novel vitamin C phosphodiesters: Stability and antioxidant activity
Morisaki, Kazuo,Ozaki, Shoichiro
, p. 123 - 138 (2007/10/03)
A novel series of hybrid L-ascorbic acid (vitamin C) phosphodiesters linked at the C-2 hydroxyl group with other biologically active substances, namely myo-inositol, arbutin, 4-hydroxy-L-proline, and glycolic acid were synthesized, and their thermal stability and reducing activity against free radicals were estimated in vitro. All of the phosphodiesters exhibited high thermal stabilities; however, their antioxidant activities in vitro were generally lower than that of vitamin C.
The absolute configuration and optical purity of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols
Aneja,Aneja,Parra
, p. 17 - 18 (2007/10/02)
The absolute configurations of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols are derived as 1D- and 1L-1,2:4,5-di-O-cyclohexylidene-myo-inositols respectively, and are reverse of the most recent literature assignments.
INVESTIGATIONS IN THE FIELD OF DERIVATIVES OF ASYMMETRICALLY SUBSTITUTED myo-INOSITOL. XXXVI. SEPARATION OF DIASTEREOMERIC CARBOHYDRATE DERIVATIVES OF myo-INOSITOL BY THE HPLC METHOD
Runova, O. B.,Krylova, V. N.,Shastina, N. S.,Eremin, S. V.,Stepanov, A. E.,Shvets, V. I.
, p. 249 - 257 (2007/10/02)
The possibility has been shown of using the HPLC method for separating diastereomeric compounds of myo-inositol obtained under the conditions of the transesterification of racemic myo-inositol derivatives with D-mannose (ethyl orthoacetate).The optically active myo-inositol derivatives obtained can be used for the synthesis of myo-inositol phosphates with various structures.
Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
, p. 729 - 738 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.
Synthesis of D- and L-myo-Inositol 1-phosphorothioate, Substrates for Inositol Monophosphatase
Baker, Graham R.,Billington, David C.,Gani, David
, p. 3895 - 3908 (2007/10/02)
The D- and L- enantiomers of myo-inositol 1-phosphorothioate have been synthesized from 2,3,4,5,6-pentakis-O-benzyl myo-inositol in 6 steps, both compounds are substrates for inositol monophosphatase.D-glucopyranose 6-phosphorothioate did not serve as a s
