Preparation of D-mannitol-C-14 and its conversion to D-fructose-1-(and 6)-C-14 by acetobacter suboxydans

Isbell, Horace S.; Karabinos, J. V.

doi:10.6028/jres.048.056

Cited by 19 publications

(5 citation statements)

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“…In the periodate oxidation of the disaccharide methyl glycoside obtained by reduction of aldobiouronic acid II 2.9 moles of periodate was consumed and 1.16 moles of formic acid was produced. These data fitted the requirements for a glucose unit linked glycosidically to a xylopyranoside unit through C (2) or C»)• Similar oxidation of the disaccharide methyl glycoside from aldobiouronic acid (1) Presented in part before the Division of Cellulose Chemistry, 128th Meeting, American Chemical Society, Minneapolis, Minn., 1955.…”

Section: Introductionmentioning

confidence: 66%

Constitution of Two Aldobiouronic Acids from Wheat Bran Hemicellulose^1,2

Adams¹,

Bishop²

1956

J. Am. Chem. Soc.

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Section: Introductionmentioning

confidence: 66%

Constitution of Two Aldobiouronic Acids from Wheat Bran Hemicellulose^1,2

Adams¹,

Bishop²

1956

J. Am. Chem. Soc.

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“…Previously, d -mannitol- 1-C 14 had been oxidized by A. suboxydans to d -fructose- 1 , 6 - C 14 [ 3 ], and the isotopic distribution in the latter compound had been determined [ 4 ]. 5 In the present study, d -mannitols labeled either with carbon-14 at C1, C2, or C3, or with tritium attached to C1, C2, or C3, were prepared and were then oxidized by A. suboxydans.…”

Section: Introduction and Discussionmentioning

confidence: 99%

“… 11 In their preparation of d -fructose- 1,6-C 14 , Isbell and Karabinos [ 3 ] determined both the total reducing-substance and the d -fructose (the latter by polarization at two temperatures). They showed that the maxima for the two occur at approximately the same time.…”

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confidence: 99%

Tritium-labeled compounds VII. Isotope effects in the oxidation of D-mannitols-C14 and D-mannitols-t to D-fructoses

Sniegoski¹,

Frush²,

Isbell³

1961

J. RES. NATL. BUR. STAN. SECT. A.

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(M ay 17, 196 1) n -Ma nni tols, la beled eit her wi t h carbo n-14 at C l , C2, or C3, o r wi t h tri tium a t tached to C l , C2, or C3, were prepa red . After oxidatio n by Acetobacter suboxydans, t he dist ribu tio n of r adi oactivity in each of t he r es ul t in g labeled n-fructoses wa det er mined . La beled nma nni tol is uni que a mong t he hexito ls in t ha t i t may be ox idi zed by A . suboxydans in eit her t he la beled or t he unl a beled p ar t of t he molecule. Excep t in t he oxidat ion of n-man ni tol-2-t, t he co mpet ing reactio ns r es ult in t he formation o f a mi xt ure of D-fr uctoses, ea ch hav in g ra di oact ivity in on e of t wo d ifferen t posit ion s. H cnce, t he iso to pe effect, k */ k, (where k * a nd k are, r es pectively, t he rate co ns tan ts for ox idatio n ill t he la beled and in t he unla beled part of t he la beled D-ma n nitol molecule) is t he ratio of t he act ivit ies at the t wo positions of t he produ ct, n-fructose.The follo win g isoto pe eff ects were fou nd for t he bacteri al oxid a t ion of la beled D-mannito ls : (1 ) for n-ma n ni tol-2-C14, k * / k = 0.93 ; (2) for n-mannito l-2-t, Ie * /k = 0.23; a nd (3) for D-ma nni to l-3-t, k */k = 0.70 . For n-m a nni to ls la beled at other positio ns, no isotop e effect was detected, s ince k */ k was uni t y . The large isotope-effect fo r n-ma nn itol-2-t is in d icat ive of rup t ure of t he C2-H bo nd in t he ra t e-d etermin in g process. It is s ugges ted t hat t he seco ndar y isoto pe-effect for t ri t iu m a t C3 indi cat es hyper co njugation of t he C3 h ydroge n ato m in t he activa ted enzy me-s ubstrate co mplex ; t he lack o f s uch effect fo r t ri t iu m at Cl may be du e to unfa vora ble s teric co ndi tions fo r hypercon ju ga t io n of t he Cl h ydroge n a to ms in the co mplex. The fo llo wing su bst a nces wer e p repa red a nd t heir isoto pic dist ribu t ions d ete rmin ed : n-fr uctose-l ,6-C" a nd n-fr uctose-l ,6-t (fr o m I-la beled n-m a nnito ls); n-fru ctose-2,5-C14 a nd n-fru ctose-5-t (from 2-la beled n-m a nni tols); and n-fr uctose-3,4-C14 a nd n-fru ctose-3,4 -t (fro m 3-1a beled D-ma nni tols). A procedure, e mploy in g n-fru ctose-J ,6-C14 as a n int ern al sta ndard , was d ev ised for t he analysis of D-fru ctose-3,4-t.

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“…With a surface: volume ratio of 1:195, Fulmer et al (1939) found that mannitol concentrations up to and including 25 per cent weight per volume (w/v) were consistently converted to fructose to the extent of 90 per cent or better of theoretical in 7 days or less. The findings of Fulmer et al (1939) were confirmed by the work of Isbell and Karabinos (1952), but only with regard to low mannitol concentrations (less than 5 per cent). As far as is known, these surfaceculture laboratory-scale investigations are the only published reports available on the conversion of mannitol to fructose by A. suboxydans.…”

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confidence: 81%

“…The conversion of D-mannitol to D-fructose by the oxidative action of A. suboxydans, which was first reported by Bertrand (1904), has also been studied but to a considerably lesser extent. Laboratory-scale studies on this conversion under surfaceculture fermentation conditions were first reported by Fulmer et al (1939) and more recently by Isbell and Karabinos (1952). With a surface: volume ratio of 1:195, Fulmer et al (1939) found that mannitol concentrations up to and including 25 per cent weight per volume (w/v) were consistently converted to fructose to the extent of 90 per cent or better of theoretical in 7 days or less.…”

mentioning

confidence: 95%