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Showing NP-Card for L-Sorbose (NP0001444)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:57 UTC
NP-MRD IDNP0001444
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Sorbose
DescriptionL-Sorbose, also known as L-sorbinose or L-xylo-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Sorbose exists in all living species, ranging from bacteria to humans. The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose (CAS: 87-79-6) Is a ketose belonging to the group of sugars known as monosaccharides. Sorbose has been found to be a metabolite of Ketogulonicigenium (PMID: 15785002 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001444 (L-Sorbose)


  Mrv1652305271900192D          

 12 12  0  0  1  0            999 V2000
   15.5117   -6.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612   -7.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9610   -6.9682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6867   -6.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2466   -6.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5321   -6.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5321   -7.7932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8177   -8.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2466   -8.2057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2466   -9.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9610   -7.7932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6755   -8.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
Download

3D MOL for NP0001444 (L-Sorbose)

HMDB0001266
     RDKit          3D
L-Sorbose
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.7116   -0.7039   -0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -0.7829    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    0.4001    0.3683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8410    1.5485    0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.4650    1.5267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -0.3086    1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.7066    0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7990   -1.0125    0.5933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.4908   -0.5324 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0854    0.4175   -1.6377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    0.4282   -0.8896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5618    1.4274   -1.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084   -1.1193   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6901   -0.7670    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101   -1.7514    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    2.2622   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.2951    2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244   -1.2235    2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -1.5774   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -1.2131    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    1.4229    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    1.3253   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -0.5448   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    1.2280   -2.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  6
 12 24  1  0
M  END
Download

3D SDF for NP0001444 (L-Sorbose)


  Mrv1652305271900192D          

 12 12  0  0  1  0            999 V2000
   15.5117   -6.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612   -7.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9610   -6.9682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6867   -6.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2466   -6.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5321   -6.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5321   -7.7932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8177   -8.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2466   -8.2057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2466   -9.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9610   -7.7932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6755   -8.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0001444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1

> <INCHI_KEY>
LKDRXBCSQODPBY-BGPJRJDNSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.051261078337298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

> <ALOGPS_LOGP>
-2.51

> <JCHEM_LOGP>
-2.7579993179999995

> <ALOGPS_LOGS>
0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.643871080491373

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.291030669254257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.450704169945884

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
36.3608

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-L-sorbopyranose

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001444 (L-Sorbose)

HMDB0001266
     RDKit          3D
L-Sorbose
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.7116   -0.7039   -0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -0.7829    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    0.4001    0.3683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8410    1.5485    0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.4650    1.5267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -0.3086    1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.7066    0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7990   -1.0125    0.5933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.4908   -0.5324 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0854    0.4175   -1.6377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069    0.4282   -0.8896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5618    1.4274   -1.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084   -1.1193   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6901   -0.7670    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101   -1.7514    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    2.2622   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.2951    2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244   -1.2235    2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -1.5774   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -1.2131    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    1.4229    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    1.3253   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -0.5448   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    1.2280   -2.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  6
 12 24  1  0
M  END
Download

PDB for NP0001444 (L-Sorbose)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      28.955 -12.604   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.554 -13.696   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.061 -13.007   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.415 -11.449   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.727 -12.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.393 -13.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.393 -14.547   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.060 -15.317   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.727 -15.317   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.727 -16.857   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      26.061 -14.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      27.394 -15.317   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    3    9   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0001444 (L-Sorbose)

COMPND    HMDB0001266
HETATM    1  O1  UNL     1      -2.712  -0.704  -0.881  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.981  -0.783   0.308  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.010   0.400   0.368  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.841   1.549   0.327  1.00  0.00           O  
HETATM    5  O3  UNL     1      -0.321   0.465   1.527  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.774  -0.309   1.686  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.468  -0.707   0.403  1.00  0.00           C  
HETATM    8  O4  UNL     1       2.799  -1.012   0.593  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.281   0.491  -0.532  1.00  0.00           C  
HETATM   10  O5  UNL     1       2.085   0.418  -1.638  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.207   0.428  -0.890  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.562   1.427  -1.768  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.608  -1.119  -0.693  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.690  -0.767   1.160  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.410  -1.751   0.254  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.380   2.262  -0.181  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.536   0.295   2.265  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.624  -1.224   2.316  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.966  -1.577  -0.058  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.030  -1.213   1.530  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.503   1.423   0.034  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.123   1.325  -2.044  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.325  -0.545  -1.441  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.145   1.228  -2.645  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4    5   11
CONECT    4   16
CONECT    5    6
CONECT    6    7   17   18
CONECT    7    8    9   19
CONECT    8   20
CONECT    9   10   11   21
CONECT   10   22
CONECT   11   12   23
CONECT   12   24
END
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SMILES for NP0001444 (L-Sorbose)

OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O
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INCHI for NP0001444 (L-Sorbose)

InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1
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View in JSmol
Synonyms
ValueSource
alpha-L-SorbopyranoseHMDB
Hex-2-uloseHMDB
L(-) Sorbose for biochemistryHMDB
L(-)-SorboseHMDB
L-(-)-SorboseHMDB
L-(-)-Sorbose 99%HMDB
L-1,3,4,5,6-Pentahydroxyhexan-2-oneHMDB
L-SorbinoseHMDB
L-Xylo-2-hexuloseHMDB
L-Xylo-hexuloseHMDB
SorbinHMDB
SorbinoseHMDB
SorboseHMDB
Xylo-hexuloseHMDB
alpha-L-Xylo-hexopyranos-2-uloseHMDB
Α-L-xylo-hexopyranos-2-uloseHMDB
Α-L-sorbopyranoseHMDB
a-L-SorbopyranoseHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameα-L-sorbopyranose
CAS Registry Number87-79-6
SMILES
OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1
InChI KeyLKDRXBCSQODPBY-BGPJRJDNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Sparganium eurycarpumLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility360 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1190 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001266
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001126
KNApSAcK IDC00019630
Chemspider ID390208
KEGG Compound IDC08356
BioCyc IDSORBOSE
BiGG IDNot Available
Wikipedia LinkSorbose
METLIN ID6121
PubChem Compound441484
PDB IDSOE
ChEBI ID10295
Good Scents IDNot Available
References
General References
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  2. Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57. [PubMed:9154994 ]
  3. Wang C, So SY, Wong KK, So WW, Chan SY: Chronic sinopulmonary disease in Chinese patients with obstructive azoospermia. J Androl. 1987 Jul-Aug;8(4):225-9. [PubMed:3624059 ]
  4. Kossi J, Peltonen J, Uotila P, Laato M: Differential effects of hexoses and sucrose, and platelet-derived growth factor isoforms on cyclooxygenase-1 and -2 mRNA expression in keloid, hypertrophic scar and granulation tissue fibroblasts. Arch Dermatol Res. 2001 Mar;293(3):126-32. [PubMed:11357226 ]
  5. Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
  6. Fukasawa M, Takayama E, Shinomiya N, Okumura A, Rokutanda M, Yamamoto N, Sakakibara R: Identification of the promoter region of human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. Biochem Biophys Res Commun. 2000 Jan 27;267(3):703-8. [PubMed:10673355 ]
  7. Le KA, Tappy L: Metabolic effects of fructose. Curr Opin Clin Nutr Metab Care. 2006 Jul;9(4):469-75. [PubMed:16778579 ]
  8. Fukasawa M, Tsuchiya T, Takayama E, Shinomiya N, Uyeda K, Sakakibara R, Seki S: Identification and characterization of the hypoxia-responsive element of the human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. J Biochem. 2004 Sep;136(3):273-7. [PubMed:15598882 ]
  9. Yanez AJ, Bertinat R, Spichiger C, Carcamo JG, de Los Angeles Garcia M, Concha II, Nualart F, Slebe JC: Novel expression of liver FBPase in Langerhans islets of human and rat pancreas. J Cell Physiol. 2005 Oct;205(1):19-24. [PubMed:15965961 ]
  10. Lee YH, Li Y, Uyeda K, Hasemann CA: Tissue-specific structure/function differentiation of the liver isoform of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase. J Biol Chem. 2003 Jan 3;278(1):523-30. Epub 2002 Oct 11. [PubMed:12379646 ]
  11. Minchenko O, Opentanova I, Minchenko D, Ogura T, Esumi H: Hypoxia induces transcription of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase-4 gene via hypoxia-inducible factor-1alpha activation. FEBS Lett. 2004 Oct 8;576(1-2):14-20. [PubMed:15474002 ]
  12. Andrade-Rocha FT: Physical analysis of ejaculate to evaluate the secretory activity of the seminal vesicles and prostate. Clin Chem Lab Med. 2005;43(11):1203-10. [PubMed:16232086 ]
  13. Roy S, Banerjee A, Pandey HC, Singh G, Kumari GL: Application of seminal germ cell morphology and semen biochemistry in the diagnosis and management of azoospermic subjects. Asian J Androl. 2001 Mar;3(1):55-62. [PubMed:11250795 ]
  14. Blakemore SJ, Aledo JC, James J, Campbell FC, Lucocq JM, Hundal HS: The GLUT5 hexose transporter is also localized to the basolateral membrane of the human jejunum. Biochem J. 1995 Jul 1;309 ( Pt 1):7-12. [PubMed:7619085 ]
  15. Abou El Fadil-Nicol F, Berger F, Descroix-Vagne M, Pansu D: Presence of sorbin in human digestive tract and endocrine digestive tumours. Gut. 2000 Feb;46(2):182-90. [PubMed:10644311 ]
  16. Faeh D, Minehira K, Schwarz JM, Periasamy R, Park S, Tappy L: Effect of fructose overfeeding and fish oil administration on hepatic de novo lipogenesis and insulin sensitivity in healthy men. Diabetes. 2005 Jul;54(7):1907-13. [PubMed:15983189 ]
  17. Atsumi T, Chesney J, Metz C, Leng L, Donnelly S, Makita Z, Mitchell R, Bucala R: High expression of inducible 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase (iPFK-2; PFKFB3) in human cancers. Cancer Res. 2002 Oct 15;62(20):5881-7. [PubMed:12384552 ]
  18. Wu LY, Juan CC, Hwang LS, Hsu YP, Ho PH, Ho LT: Green tea supplementation ameliorates insulin resistance and increases glucose transporter IV content in a fructose-fed rat model. Eur J Nutr. 2004 Apr;43(2):116-24. Epub 2004 Jan 6. [PubMed:15083319 ]
  19. Ludwig M, Vidal A, Diemer T, Pabst W, Failing K, Weidner W: Seminal secretory capacity of the male accessory sex glands in chronic pelvic pain syndrome (CPPS)/chronic prostatitis with special focus on the new prostatitis classification. Eur Urol. 2002 Jul;42(1):24-8. [PubMed:12121725 ]
  20. Massucco P, Mattiello L, Russo I, Traversa M, Doronzo G, Anfossi G, Trovati M: High glucose rapidly activates the nitric oxide/cyclic nucleotide pathway in human platelets via an osmotic mechanism. Thromb Haemost. 2005 Mar;93(3):517-26. [PubMed:15735804 ]
  21. Sugisawa T, Miyazaki T, Hoshino T: Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025. Biosci Biotechnol Biochem. 2005 Mar;69(3):659-62. doi: 10.1271/bbb.69.659. [PubMed:15785002 ]