Mannitol-l-phosphate

L.A., Nadal, L, Monedero, V. et al (2010) Sorbitol production om lactose by engineered Lactobacillus casei deficient in sorbitol transport system and mannitol-l-phosphate dehydrogenase. Appl. Microbiol Biotechnol, 85, 1915-1922. 

Glucose-phosphate isomerase is one of the best studied enzymes catalyzing the interconversion of aldo- and ketohexose phosphates. An active site carboxyl group is a possible candidate for the base catalyzing the intramolecular proton transfer reaction. The affinity label 1,2-anhydro-D-mannitol 6-phosphate (8) inactivates the enzyme by forming an ester linkage between C-l of the affinity label and an active site carboxyl of a glutamic acid residue (98). 

The alcoholysis of the cyclic phosphate of catechol by alditols can lead, after acid hydrolysis of intermediate, cyclic phosphates, to the selective formation of phosphoric esters of the primary hydroxyl groups in the alditols. Thus, erythritol and D-mannitol afford, after chromatographic purification of the reaction products, their 1-phosphates in yields of 31 and 38%, respectively.217 The method was used to convert riboflavine into riboflavine 5 -phosphate.218 1-Deoxy-1-fluoro-L-glycerol has been converted into the 3-(dibenzyl phosphate) in 54% yield by selective reaction with dibenzyl phosphorochloridate. 219... 

Mannitol hexanitrate is obtained by nitration of mannitol with mixed nitric and sulfuric acids. Similarly, nitration of sorbitol using mixed acid produces the hexanitrate when the reaction is conducted at 0—3°C and at —10 to —75°C, the main product is sorbitol pentanitrate (117). Xylitol, ribitol, and L-arabinitol are converted to the pentanitrates by fuming nitric acid and acetic anhydride (118). Phosphate esters of sugar alcohols are obtained by the action of phosphorus oxychloride (119) and by alcoholysis of organic phosphates (120). The 1,6-dibenzene sulfonate of D-mannitol is obtained by the action of benzene sulfonyl chloride in pyridine at 0°C (121). To obtain 1,6-dimethanesulfonyl-D-mannitol free from anhydrides and other by-products, after similar sulfonation with methane sulfonyl chloride and pyridine the remaining hydroxyl groups are acetylated with acetic anhydride and the insoluble acetyl derivative is separated, followed by deacetylation with hydrogen chloride in methanol (122). Alkyl sulfate esters of polyhydric alcohols result from the action of sulfur trioxide—trialkyl phosphates as in the reaction of sorbitol at 34—40°C with sulfur trioxide—triethyl phosphate to form sorbitol hexa(ethylsulfate) (123). 

To be reconstituted with 1 mL sterile WFI containing 1.0 mg Poloxamer 188 (0.15mg/mL) Per 5mg vial 33.0mg mannitol 3.0mg sodium phosphate monobasic monohydrate 8.8 mg sodium phosphate dibasic heptahydrate Per vial 10.6 mg mannitol IV 15.9mg/mL L-alanine 12.6-14.3 mg of dibasic sodium phosphate... 

Figure 14.4 Chromatograms of excipients in different classes. Plot (a) represents excipients in surfactant class. The curves from the bottom are blank, cremorphor 35, SLS, Tween 80 and VE, respectively. Plot (b) represents excipients in the filler class. The curves from the bottom are blank, DCP, lactose, mannitol, MCC and SWS, respectively. In both plots, the sample solvent and mobile phase used are 20% ACN-80% pH 2, 25 mM phosphate buffer and a gradient from 30% ACN-70% pH 2, 25 mM phosphate buffer to 80% ACN-20% pH 2, 25 mM phosphate buffer, respectively. The samples were injected at 1800 p,L onto a Zorbax SB-Cg, 4.6 x 150 mm, 3.5 xm column at 35°C with a flow rate of 1 mL/min. The detection was at 210 nm.

The use of polyols such as pentaerythritol, mannitol, or sorbitol as classical char formers in intumescent formulations for thermoplastics is associated with migration and water solubility problems. Moreover, these additives are often not compatible with the polymeric matrix and the mechanical properties of the formulations are then very poor. Those problems can be solved (at least partially) by the synthesis of additives that concentrate the three intumescent FR elements in one material, as suggested by the pioneering work of Halpern.29 b-MAP (4) (melamine salt of 3,9-dihydroxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]-undecane-3,9-dioxide) and Melabis (5) (melamine salt of bis(l-oxo-2,6,7-trioxa-l-phosphabicyclo[2.2.2]octan-4-ylmethanol)phosphate) were synthesized from pentaerythritol (2), melamine (3), and phosphoryl trichloride (1) (Figure 6.4). They were found to be more effective to fire retard PP than standard halogen-antimony FR. 

Rather uncommon are the two pyruvic acetal structures which have been identified in Klebsiella K12 capsular polysaccharides and in the teichoic acid of bacterium NCTC 9742 [10]. In the former case, a 4,5-0-(l-carboxyethylidene)- -D-galactofuranosyl residue was found at the side chain terminus of the hexa-saccharide repeating unit. In the latter case, the teichoic acid contains intra-catenally bound 2,3-0-(l-carboxyethylidene)-D-mannitol phosphate. No data about the configuration of these pyruvic acetals are available. 

Fig. 14 The effect of excipients on the storage stability of freeze-dried human growth hormone (hGH). Samples were stored for 1 month at 40°C. Solid bars aggregation (primarily dimer), shaded bar = chemical degradation via methionine oxidation and asparagine deamidation. The glass transition temperatures of the initial freeze-dried formulations are given above the bars when a glass transition temperature could be measured by DSC. The glycine mannitol formulation is a weight ratio of hGH glycine mannitol of 1 1 5, the dextran formulation is 1 6 hGH dextran 40, none means no stabilizer, and the others are 1 1 hGH stabi-lizer. All formulations contain sodium phosphate buffer (pH 7.4) at 15% of the hGH content. Initial moisture contents are all 1%. (From Ref l)...

If the liposome preparations are intended to be stored for longer time periods, they may be frozen or lyophilized, provided that they are prepared in a phosphate buffer that contains a cryoprotectant. We use an iso-osmolar phosphate-mannitol buffer of the following composition 20 mM phosphate buffer (0.53 g/L KH PO plus 2.87 g/L Na2HP0 2Hp) plus 230 mM mannitol (42.0 g/L mannitol), (PB-Man)... 

Preparation. Fischer and Baer employed the glycol cleavage of l,2 5,6-di-0-isopropylidene-D-mannitol, followed by acid hydrolysis, to provide d-glyceraldehyde.13 A most convenient preparation is that of Perlin,14 who oxidized D-fructose with a limited proportion of lead tetraacetate, and hydrolyzed the resulting derivative. D-Glyceraldehyde 3-phosphate has been synthesized.15... 

D-l-Deoxy-l-fluoroglycerol 3-phosphate (59), a potential anticancer agent, has been prepared from D-mannitol (60) by a stereospecific route which should be suitable for the synthesis of the L-isomer of (59).i 8 Transformation of (60) into D-l-tosyl-2,3-0-isopropylideneglycerol, followed by displacement of tosyl ion by fluoride ion, removal of the isopropylidene group, and treatment with dibenzyl phosphorochloridate gave the dibenzyl ester of (59). A DL-mixture of this dibenzyl ester was... 

---