Chemical Identification.

Spectroscopic Properties
Mass spectrum
H NMR
C13 NMR
IR
UV
X-ray crystallography

Physical properties: (Source of all information except CAS number Beilstein)

Chemical name:

 5- Acetamido- 2, 6- anhydro- 3, 4, 5- trideoxy- 4- guanidino- D- glycero- D- galacto- non- 2- enonic acid
Synonyms: Zanamivir, GG167, 4-guanidino-Neu5Ac2en and 2,3- Didehydro- 2, 4- dideoxy- 4- guanidino- N- acetyl- D- neuraminic acid
Empirical formula:

C12H20N4O7
Structural formula:

Molecular weight: 332.31g
Beilstein number: 7083099
Normal State: Powder
Colour: White to 'off white'
Melting point: 325oC
Optical rotary power2: Type [µ]

Conc: 0.9g/100ml

Solvent: H2O

Optical rotary power: 41 deg

Wavelength: 589nm

Temp: 20oC
 CAS number: 139110-80-8 
Solubility: 18mg/mL in water at 20oC

 

SMILES: OC[C@@H](O)[C@@H](O)[C@@]1([H])[C@H]([C@@H]([H])C(C)=O)[C@@H](NC(N)=N)C=C(C(O)=O)O1

Visit the Corina website at http://www.2.ccc.uni-erlangen.de/services/3d.html, paste in the SMILES string shown above and press submit. This will give you a three-dimensional version of Relenza which can be manipulated. 

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Spectroscopic properties:
Mass spectrum:

The product ion mass spectrum of zanamivir (using a stable iostope anologue of zanamivir as an internal standard) is shown below. Click on the image to enlarge it and use the 'identification' button on the contents bar to return to this page.

massspec.gif (7017 bytes)

 

1H NMR13:
Hydrogen Chemical shift /ppm
(1H, d, 3-H) 5.53
(2H, 2dd, 4- and 6-H) 4.50 - 4.38
(1H, dd, 5-H) 4.21
(2H, dd+ddd, 9-Ha and 8-H) 4.00-3.88
(2H, 2dd, 9-Hb and 7-H) 3.70-3.62
(3H, s,  Ac) 2.05

 

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13C NMR12:
Carbon Shift /ppm
(C=O, Ac) 177.3
(C-1) 172.1
(guanidino) 159.9
(C-2) 152.1
(C-3) 106.8
(C-6) 78.3
(C-8) 72.6
(C-7) 71.0
(C-9) 65.9
(C-4) 54.0
(C-5) 50.6
(Me) 24.8

 

IR spectra13:

The following peaks are present in the IR spectra of Relenza: 3332cm-1, 1676cm-1, 1600cm-1, 1560cm-1, 1394cm-1, 1322cm-1 and 1281cm-1.

 

UV spectra13:

The maximum peak is 235nm giving E = 199 dm-3 mol-1cm-1

 

X-Ray crystallography:

For information on this (and more) please visit: http://www.chemsoc.org/exemplarchem/entries/hamblin9/