Sucrose → D-(-)-Fructose

HRID 2275690Notes

Reaction equation

HRID 2275690 reaction equation
NC1C=CC=CC=1.[CH2:8]([OH:30])[C@H:9]1[O:14][C@H:13]([O:15]C[C@H]2OC(O)(CO)[C@@H](O)[C@@H]2O)[C@H:12]([OH:27])[C@@H:11]([OH:28])[C@@H:10]1[OH:29].[CH2:31]([OH:53])[C@H:32]1[O:37][C@H:36]([O:38]CC([C@@H](O)[C@H](O)[C@H](O)CO)=O)[C@H:35]([OH:50])[C@@H:34]([OH:51])[C@@H:33]1[OH:52].[CH2:54]([OH:76])[C@H:55]1[O:60][C@H:59]([O:61][C@:62]2([CH2:71][OH:72])[O:66][C@H:65]([CH2:67][OH:68])[C@@H:64]([OH:69])[C@@H:63]2[OH:70])[C@H:58]([OH:73])[C@@H:57]([OH:74])[C@@H:56]1[OH:75]>C(OC(=O)C)C>[O:15]=[CH:13][C@@H:12]([C@H:11]([C@@H:10]([C@@H:9]([CH2:8][OH:30])[OH:14])[OH:29])[OH:28])[OH:27].[OH:53][CH2:31][C:32]([C@H:33]([C@@H:34]([C@@H:35]([CH2:36][OH:38])[OH:50])[OH:51])[OH:52])=[O:37].[CH2:54]([OH:76])[C@H:55]1[O:60][C@H:59]([O:61][C@:62]2([CH2:71][OH:72])[O:66][C@H:65]([CH2:67][OH:68])[C@@H:64]([OH:69])[C@@H:63]2[OH:70])[C@H:58]([OH:73])[C@@H:57]([OH:74])[C@@H:56]1[OH:75]

Participants

8

Reactant 4

HCID 5988SucroseHCID 6115AnilineHCID 162104TrehaluloseHCID 439559GlyTouCan:G36918VO

Product 3

HCID 5984D-(-)-FructoseHCID 5988SucroseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

TLC was performed by spotting 3 microliters of the supernatants of the growth media onto AL SIL G silica gel plates (Whatman) and developed twice in a solvent consisting of 3 parts ethylacetate: 3 parts acetic acid: 1 part distilled water. After drying, the plates were sprayed with a dye mixture consisting of 4 milliliters aniline, 4 g diphenylamine, 200 milliliters acetone, and 30 milliliters 80% phosphoric acid. Isomaltulose and trehalulose were distinguished from other sugars, such as sucrose, by their relative mobility and by the distinct colors produced when they reacted with aniline dye. Greenish yellow indicates the presence of isomaltulose, red indicates the presence of trehalulose, and brown/black indicates the presence of sucrose. The monosaccharides, glucose and fructose, produced by hydrolysis of sucrose were blue or red-orange respectively.

Workup

  1. distillation3 parts acetic acid: 1 part distilled water
  2. customAfter drying
  3. customproduced when they

Sources & evidence

ORD record
ord-160651471442458288551188b9eae315
Source dataset
uspto-grants-2015_09
Patent number
US09127287B2

Reaction notes

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