Amino Acid

Serine 

Chemical Features:

• Non-aromatic hydroxyl
• Hydrophilic due to the hydrogen bonding capacity of the hydroxyl group
• Molecular formula: C3H7NO3
• Molecular Weight: 105 g
• Appearance: white crystals or powder
• Soluble in water
• Melting point: 246 degrees Celsius

pKa Values:

• 2.21 (carboxyl)
• 9.15 (amino)

Isoelectric Point: (pH at which this amino acid carries no net electrical charge)

• 5.68

Functional Group:

• Hydroxyl

NMR Info:

• Three main peaks: Peak at 4.65, Peak at 3.75, Peak at 3.65
• Pictures can be found at: https://sharepoint.cisat.jmu.edu/isat/klevicca/Web/Amino/Serine_2001/9.htm

IR Info:

A better picture of the IR spectroscopy can be found at: http://webbook.nist.gov/cgi/cbook.cgi?Spec=C56451&Index=0&Type=IR&Large=on

Reaction Info:

• The biosynthesis of serine starts with the oxidation of 3-phosphoglycerate to 3-phosphohydroxypyruvate and NADH Reductive amination of this ketone followed by hydrolysis gives serine. Serine hydroxymethyltransferase catalyzes the reversible, simultaneous conversion of L-serine to glycine. 
• Racemic serine can be prepared from methly acrylate via several steps. It is also naturally produced when UV light illuminates simple ices such as a combination of water, methanol, hydrogen cyanide, and ammonia, suggesting that it may be easily produced in cold regions of space. 

Small Polypeptide:

References:

http://www.biology.arizona.edu/biochemistry/problem_sets/aa/serine.html

http://en.wikipedia.org/wiki/Serine

http://www.chemie.fu-berlin.de/chemistry/bio/aminoacid/serin_en.html

https://sharepoint.cisat.jmu.edu/isat/klevicca/Web/Amino/Serine_2001/9.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C56451&Index=0&Type=IR&Large=on

Electrophilic Aromatic Substitution from a Peer-Reviewed Journal

Aromatic compounds have multiple double bonds so the compounds cannot undergo addition reactions. Therefore, they react by electrophilic aromatic substitution reactions. The aromaticity of the ring system is preserved. I found a peer-reviewed journal through Ebsco entitled, Reaction of N,N-Dimethylaniline with N-Cyanoazoles according to Electrophilic Aromatic Substitution Pattern, that discusses an electrophilic aromatic substitution reaction. This article was found in the Russian Journal of Organic Chemistry.


N-Cyanoazoles are highly reactive organic compounds. These compounds are important intermediate products that are involved in the synthesis of numerous derivatives containing an azole ring. N-cyanoazoles are capable of acting as electrophilic reagents in elctrophlic aromatic substitution reactions because of the high polarity of the cyano group.

This journal reported on the synthesis of some imines by electrophilic aromatic substituion of hydrogen in N,N-dimethylaniline by N-cyanoimidazole,  N-cyanobenzimidazole,  N-cyano-1,2,3-benzotriazole, and N-cyano-2-methylimidazoles. These N-cyanoazoles, Ia–Id, were prepared according to certain standard procedures.

They demonstrated that the previously listed N-cyanoazoles reacted with N,N-dimethylaniline in the presence  of anhydrous aluminum bromide to give para-substituted imines in good yields (65-74%). Nitrobenzene was found to be appropriate solvent for carrying out these reaction. reactions. The high polarity and dissolving
power of nitrobenzene ensure the homogeneity of the reaction mixture. However, nitrobenzene is not involved in the reaction because of the presence of a strong electron-withdrawing nitro group in its molecule.


Here is the picture of the substitution:

Reference:
Chunaev, A. O., Stepanov, E. A., & Purygin, P. P. (2010). Reaction of N, N-dimethylaniline with N-cyanoazoles according to electrophilic aromatic substitution pattern. Russian Journal of Organic Chemistry, 46(3), 459-460. doi:10.1134/S1070428010030309