Sucrose
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C12H22O11
Molecular Weight: 342.296
InChI= 1/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-
12/h4-11,13-20H,1-3H2
IUPAC Name:  Hex-2-ulofuranosyl hexopyranoside
CAS Number: 57-50-1
PubChem: 1115
NMRShiftDB: 10017706
Spectrometer: Varian INOVA 600 MHz
Solvent: D2O
Sample Concentration: 4 mg
Provided by:  Dr. Dimitris Argyropoulos, Varian Deutschland GmbH

*.fid/text file specifies: 4 mg Sucrose in D2O Inova 600 MHz
*.fidnpntswrfp-rflnisw1rfp1-rfl1time
PROTON830242194.911601.4231 s
CARBON26202819212060.916787.465 h 53 m
DQFCOSY409622194.911601.425122194.911601.421 h 11 m
gHMBC409642194.911601.4251212063.906785.9455 m 59 s
gHSQC102422194.911601.4225612062.736786.5328 m 24 s


1D Proton Spectrum:

1D Proton Spectrum


1D Carbon Spectrum (Deuterated Solvent Resonances Subtracted):

1D Carbon Spectrum


 

Automated VerifyIt Proton Assignments:

Proton Assignments
 

Automated VerifyIt Carbon Assignments:

Carbon Assignments

Top 10 FindIt Molecular Structures Consistent With Molecular Formula and Proton Resonances:

The correct structure is at position 3.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.986389 (  165577)    2: 0.985732 (  152120)    3: 0.985260 (    1115)
    4: 0.985213 (  193522)    5: 0.983957 (  129887)    6: 0.983866 (  219660)
    7: 0.983819 ( 3083571)    8: 0.983713 ( 6337161)    9: 0.983252 (  107148)
   10: 0.982605 (  131122)
			

Top 10 FindIt Molecular Structures Consistent With Proton and Carbon Resonances:

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.965520 (    1115)    2: 0.961349 (    1116)    3: 0.954740 (  644101)
    4: 0.953963 ( 6337101)    5: 0.948653 ( 3411519)    6: 0.948494 ( 4631010)
    7: 0.945573 (  126987)    8: 0.935207 (  242530)    9: 0.934038 ( 4631608)
   10: 0.929960 ( 4138758)
			

2D Multiplicity-Edited HSQC Spectrum:

2D Multiplicity-Edited HSQC Spectrum

Determined HSQC Correlations:

Determined HSQC Correlations

Top 10 FindIt Molecular Structures Consistent With Proton and Protonated Carbon (HSQC) Resonances:

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.965520 (    1115)    2: 0.961349 (    1116)    3: 0.954740 (  644101)
    4: 0.953963 ( 6337101)    5: 0.948653 ( 3411519)    6: 0.948494 ( 4631010)
    7: 0.945573 (  126987)    8: 0.935207 (  242530)    9: 0.934038 ( 4631608)
   10: 0.929960 ( 4138758)
			

2D DQF-COSY Spectrum:

2D DQF-COSY Spectrum

AssembleIt HSQC & DQF-COSY Derived Carbon-Carbon Correlations:

AssembleIt HSQC & DQF-COSY Derived Correlations

2D HMBC Spectrum:

2D HMBC Spectrum

AssembleIt HSQC, HMBC & DQF-COSY Derived Correlations:

AssembleIt Derived Correlations

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

AssembleIt Derived Structure   Most likely structure (out of 125 possible ones) by agreement with carbon chemical shift prediction

Comments:

FindIt identifies the correct structure from the proton and carbon resonances.

The full sucrose structure elucidation benefits from the numerous oxygens in the molecule causing good separations among carbon and proton shifts. As a result, six out of ten carbon-carbon bonds are derivable from the DQF-COSY spectrum. (Both bonds to the unprotonated 103.7 ppm carbon are unobservable. Two further bonds have ambiguous proton assignments.)

The negative side of the numerous oxygen atoms in sucrose is that they are not observable by NMR. The resulting small number of observable correlations leads to more possible structures. The best derived structure above shows an oxygen bonded to the 103.7 ppm carbon and one bonded to the 81.36 ppm carbon. This is actually the same oxygen atom. This ether bridge is not detected as no HMBC correlation across this bridge was observed.


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