N-acetylneuraminic acid

N-acetylneuraminic acid

formula | C_11H_19NO_9 name | N-acetylneuraminic acid IUPAC name | (2S, 4S, 5R, 6R)-5-acetamido-2, 4-dihydroxy-6-[(1R, 2R)-1, 2, 3-trihydroxypropyl]-2-tetrahydropyrancarboxylic acid alternate names | (2S, 4S, 5R, 6R)-5-acetamido-2, 4-dihydroxy-6-[(1R, 2R)-1, 2, 3-trihydroxypropyl]oxane-2-carboxylic acid | (2S, 4S, 5R, 6R)-5-acetamido-2, 4-dihydroxy-6-[(1R, 2R)-1, 2, 3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid | lactaminic acid | N-acetylneuraminic acid from escherichia coli | N-acetylsialic acid | NANA | sialic acid mass fractions | C (carbon) 42.7% | H (hydrogen) 6.19% | N (nitrogen) 4.53% | O (oxygen) 46.6%

Draw the Lewis structure of N-acetylneuraminic acid. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 11 n_C, val + 19 n_H, val + n_N, val + 9 n_O, val = 122 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 11 n_C, full + 19 n_H, full + n_N, full + 9 n_O, full = 206 Subtracting these two numbers shows that 206 - 122 = 84 bonding electrons are needed. Each bond has two electrons, so in addition to the 40 bonds already present in the diagram add 2 bonds. To minimize formal charge oxygen wants 2 bonds and carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 2 bonds by pairing electrons between adjacent highlighted atoms: Answer: | |

3D structure

molar mass | 309.27 g/mol phase | solid (at STP) melting point | 185 °C solubility in water | very soluble

CAS number | 131-48-6 Beilstein number | 1716283 PubChem CID number | 445063 PubChem SID number | 24888394 SMILES identifier | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O InChI identifier | InChI=1/C11H19NO9/c1-4(14)12-7-5(15)2-11(20, 10(18)19)21-9(7)8(17)6(16)3-13/h5-9, 13, 15-17, 20H, 2-3H2, 1H3, (H, 12, 14)(H, 18, 19)/t5-, 6+, 7+, 8+, 9+, 11-/m0/s1/f/h12, 18H MDL number | MFCD00006620

flash point | 184 °C