D- -2,3-Butanediol

Butanediol is a constituent of wine and an important neutral compound formed by yeast fermentation of carbohydrates. Saccharomyces cerevisiae produces mainly D(-)-2,3-butanediol and small amount of the meso form. Wines that had undergone malolactic fermentation contained traces of L(+)-2,3-butanediol which was absent from wines that had not undergone malolactic fermentation (Herold et al. 1995). 

Siemerink MAJ, Kuit W, Lopez Contreras AM, Eggink G, van der Oost J, Kengen SWM. (2011). D-2,3-Butanediol production due to heterologous expression of an acetoin reductase in Clostridium acetobutylicum. Appl Environ Microbiol, 11, 2582-2588. 

Wang Q, Chen T, Zhao X, Chamu J. (2012b). Metabolic engineering of thermophilic Bacillus licheniformis for chiral pure D-2,3-butanediol production. Biotechnol Bioeng, 109, 1610-1621. 

Figure 15.11 (a) Total ion clnomatogram of a Grob test mixture obtained on an Rtx-1701 column, and (b) re-injection of the entire clnomatogram on to an Rtx-5 column. Peak identification is as follows a, 2,3-butanediol b, decane c, undecane d, 1-octanol e, nonanal f, 2,6-dimethylphenol g, 2-ethylhexanoic acid h, 2,6-dimethylaniline i, decanoic acid methyl ester ], dicyclohexylamine k, undecanoic acid, methyl ester 1, dodecanoic acid, methyl ester. Adapted from Journal of High Resolution Chromatography, 21, M. J. Tomlinson and C. L. Wilkins, Evaluation of a semi-automated multidimensional gas chromatography-infrared-mass specti ometry system for initant analysis , pp. 347-354, 1998, with permission from Wiley-VCH. 

BUTANAL, l-d—2-METHYL-, 51, 31 erythro-2,3-Butanediol monomesylate, by reaction of trans-2-butene oxide with methanesulfonic acid, 51, 11 3,5,1,7-[1,2,3,4]Butanetetrayl-naphthalene, decahydro-, 53, 30... 

Figure 20. Simultaneous enantiomer separation of various classes of compounds ( Schurig test mixture 184) on CP-Cyclodextrin-/3-2,3,6-M-19 (permethylatcd /3-cyclodextrin in OV-1701) [25 m x 0.25 mm (i.d.) column, 70°C for 5 min followed by 3cC/miu, 0.65 bar hydrogen]143. 1+2 2,6,6-trimethylbicy-clo[3.1.1]hept-2-ene (x-pinene), 3 ( + )-(lJR)-//ms-2,6,6-trimethylbicyclo[3.1. l]heptane (pinane), 4 (-)-(lS )-fra/M-pinanc. 5 (-)-(lS)-fw-pinane, 6 ( + )-(l/J)-cw-pinane, 7 + 8 2,3-butancdiol. 9 meso-2,3-butanediol, 10 + 11 tetrahydro-5-methyl-2-furanone (y-valerolactone). 12 + 13 1-phenylethanaminc. 14 + 15 1-phenylethanol, 16 + 17 2-ethylhexanoic acid.

Patients with propionic or methylmalonic acidemia also secrete 2,3-butanediols (d-,l- or meso) and usually also 1,2-propandiol in their urine. Secretion of 1,2-propanediol is also observed during... 

Exercise 15-35 How would you synthesize (a) meso-2,3-butanediol and (b) d,l-2,3-butanediol from c/s-2-butene ... 

It has been found that meso- and D,L-2,3-butanediols give different mixtures of 2-butanone and 2-methylpropanal on treatment with sulfuric acid. From consideration of the influence of steric hindrance on the detailed mechanism of the reaction, predict which butanediol diastereomer will give more 2-methylbutanal. (The vital stage of the reaction is likely to be where the migrating group is halfway between the old and new positions.)... 

The investigations of Lucas and his coworkers with 2,3-disubstituted butanes have contributed much to the clarification of the mechanism of ring closure and ring opening of ethylene oxides and ethylene imines. D-Mreo-2,3-Butanediol (XV) is converted into a chlorohydrin (XVII) via the diacetate (XVI).24 In the formation of the chlorohydrin (XVII) a Walden inversion occurs.26 The dehydrochlorination of XVII with... 

D- and L-2,3-Butanediol. (R)-( + )-t Butyl (p-tolylsulfmy l)acetate. Cobaltacyclopentane-2-ones. 

We have excluded pathways which might involve concerted decomposition of dioxyphosphoranes to cyclic ethers with retention of stereochemistry at least for symmetrical 1,2-diols by examining the reaction of d, l-2,3-butanediol with DTPP. The C NMR spectrum of the reaction mixture is consistent only with the cis epoxide exhibiting resonances at 6 12.9 and 52.4 ppm. 

Biebl, H., Zeng, A.P., Menzel, K. and Deckwer, W.D. 1998. Fermentation of Glycerol to 1,3-Propanediol and 2,3-Butanediol by Klebsiella Pneumoniae. Appl. Microbiol. Biotechnol., 50,... 

Figure 2. CD spectra obtained within the n->w band system of the carbonyl chromophore upon dissolution of (a) acetone, (b) acetic acid, (c) acetamide, and (d) urea in (2R,3R)-2,3-butanediol (data adapted from reference [7]).

One instance where correlation with cuprammonium data appears possible is the reaction between adjacent cis glycol groups and acetone to form isopropylidene derivatives. Although data on the kinetics and equilibria of isopropylidene formation are too meager to prove that reactivity with acetone parallels reactivity with cuprammonium, isolated observations support such a supposition. Knauf, Hann, and Hudson12 have noted the ease of formation of the acetone derivatives of D-mannosan, and this is one of the substances most reactive toward cuprammonium.6 Tipson13 has noted that the optically active 2,3-butanediols react with acetone more readily than the meso form, and this is the order in which these substances react with cuprammonium.14... 

Fages, J., Mulard, D., Rouquet, J.J., and Wilhelm, J.L., 2,3-Butanediol production from Jerusalem artichoke, Helianthus tuberosus, by Bacillus polymyxa ATCC 12321. Optimization of kL a profile, Appl. Microbiol. Biotechnol., 25, 197-202, 1986. 

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