Chiro-inositol

C15H3i5N405 3.5 H20 0-(2,6-Diamino-2,3,4,6-tetradeoxy-6-C-methyI-a - d - en/thro-hexopyranosyl) - (1 — 4) - l - 3 - amino -1,3,6- trideoxy -1 -methoxy-6-(methylamino)-chiro-inositol, hydrate (fortimicin B, hydrate) (FORTBH)52... 

There are two main points of interest. First, the extent of inversion varied over a wide range, and second, the high degree of inversion found for the aminodeoxy-scyiio- (46) and 3-amino-3-deoxy-chiro-inositol acetates was in marked contrast to the predominant retention of configuration observed in the deamination of simple, equatorial amines. 

Chemical Name L-chiro-Inositol, 4-amino-l-((aminoacetyl)methylamino)-l,4-dideoxy-3-0-(2,6-diamino-2,3,4,6,7-pentadeoxy-p-L-lyxo-heptopyranosyl)-6-0-methyl-, sulfate (1 2)... 

Quercitol (= Acorn sugar 2-Deoxy-D-chiro-inositol) (cyclitol) Quercus robur (oak) (Fagaceae) [acorn], Chamaerops humilis (Palmae) [leaf], Mimusops elengii (Sapotaceae) Sweet... 

An unusual structural feature from the inositol perspective is the derivatiza-tion of the 2-hydroxyl group of inositol by a long chain fatty acid (palmitic acid). In many mature GPI-proteins, the palmatoyl side chain is not present the palmatoyl chain is added during the biosynthesis of GPI and removed after the GPI anchor is attached to the protein during posttranslational modification. Although the wyo-isomer of inositol is the most prevalent form in GPI molecules, the presence of chiro-inositol has also been detected. 

ADMET polymers containing D-chiro-inositol have been prepared by polymerizing the acetonide-protected inositol diene followed by deprotection to the D-c/z/ro-inositol containing polymer [171]. Synthesis of the monomer precursor was performed using whole-cell fermentation of bromobenzene with... 

Deoxy-chiro-inositol 1,2-0-Isopropylidene-4-C-methyl-4-nitro- E21b, 1791 (0-SiR3-6,7-dideoxy— 2,3-O-isopropyli-den — 6-N 02 — heptofuranoside/ R4NF)... 

SYNS ANTIBIOTIC SF2052 SULFATE 1-CHIRO-INOSITOL, 4-AMINO-l,4-DIDEOXY-3-o-(2,6-DIAMINO-2,3,4,6,7-PENTADEOXY-P-l-LYXO-HEPTOPYRANOSYL)-6-o-METHYL-l -(2-(FORMIMIDOYLAMINO)-N-METHYL-ACETAMIDO)-, SULFATE (1 2),HYDRATE SF-2052 SULFATE... 

Adenosine substituted on 5 -0 by a (-)chiro-inositol L-gulosamine and L-serine unit Adenomycin (5. griseoflavus) 80TL3203 ... 

C6H1205 2-deoxy-D-chiro-inositol 488-73-3 13.00 1.5845 1 8845 C6H13N03 DL-2-isopropylserine 7522-43-2 25.00 1.0476 2... 

C6H1206 L-chiro-inositol 551-72-4 20.90 1.5817 2 8891 C6H14CIN cyclohexyl amine hydrochloride 4998-76-9 100 25 ... 

The enol acetate 243 affords the Perrier product 244, a key compound to L-chiro-inositol polyphophates [201]. The Perrier cyclization of 245 is useful for the preparation of the key intermediate to glycosylphophetidylinositols [202] (O Scheme 52). 

Larner, J. D-chiro-inositol - Its functional role in insulin action and its deficit in insulin resistance. Int. J. Exp. Diah. Res., 2002, 3, 47-60. 

Fonteles, M.C., Almeida, M.Q., and Larner, J. Antihyperglycemic effects of 3-O-methyl-D-cliiro-inositol and D-chiro-inositol associated with manganese in streptozotocin diabetic rats. Horm. Metab. Res., 2000, 32, 129-132. 

J. Insulin second messengers synthesis of 6-0-(2-amino-2-deoxy-a-D-glucopyrano-sylJ-D-chiro-inositol-l-phosphate. Tetrahedron, Lett., 1993, 34, 7869-7872. 

Par, Y., Hong, Y., Kim, S., Piccariello, T, Farese, R.V., and Larner, J. In vivo chiro-inositol metabohsm in the rat a defect in chiro-inositol synthesis from myoinositol and an increased incorporation of chiro-[ H]inositol into phospholipid in the Goto-Kakizaki (GK) rat. Mol. Cells, 1998, 8, 301-309. 

Asplin, I., Galasko, G., and Larner, J. chiro-inositol deficiency and insulin resistance a comparison of the chiro-inositol-and the myo-inositol-containing insulin mediators isolated from urine, hemodia-lysate, and muscle of control and type II diabetic subjects. Proc. Natl. Acad. Sci. USA, 1993, 90,. 5924—.5928. 

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