NMRanalyst Sample Application: Sucrose

Sucrose
NMRanalyst Sample Application

NMRanalyst

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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
*.fid	np	nt	sw	rfp-rfl	ni	sw1	rfp1-rfl1	time

PROTON	8302	4	2194.91	1601.42				31 s
CARBON	26202	8192	12060.91	6787.46				5 h 53 m
DQFCOSY	4096	2	2194.91	1601.42	512	2194.91	1601.42	1 h 11 m
gHMBC	4096	4	2194.91	1601.42	512	12063.90	6785.94	55 m 59 s
gHSQC	1024	2	2194.91	1601.42	256	12062.73	6786.53	28 m 24 s

1D Proton Spectrum:

1D Carbon Spectrum (Deuterated Solvent Resonances Subtracted):

Automated VerifyIt Proton Assignments:

Automated VerifyIt Carbon Assignments:

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

The correct structure is at position 3.


 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.


 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:

Determined HSQC Correlations:

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

The correct structure is at position 1.


 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:

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

AssembleIt HSQC & DQF-COSY Derived Correlations

2D HMBC Spectrum:

AssembleIt HSQC, HMBC & DQF-COSY Derived Correlations:

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

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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