Glutamine

Figure 1: The Glutamine Amino Acid¹



Glutamine has been studied extensively over the past 10-15 years and has been shown to be useful in treatment of serious illness, injury, trauma, burns, and wound healing for postoperative patients.¹ Glutamine is also marketed as a supplement used for muscle growth in weightlifting and bodybuilding.² Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body and one of the few amino acids that directly cross the blood-brain barrier. In the body, it is found circulating in the blood as well as stored in the skeletal muscles.¹

Dietary sources of Glutamine include beef, chicken, fish, eggs, milk, wheat, dairy products, cabbage, beets, beans, spinach, vegetable juices, and fermented foods (tofu). ² Glutamine is synthesized by the enzyme glutamine synthetase from glutamate and ammonia. The most relevant glutamine-producing tissue is the muscle mass, accounting for about 90% of all glutamine synthesized.³

The alpha-carboxylic acid functional group of glutamine has a pK_a value of 2.13 and the alpha-amino group has a pK_a value of 9.13. Glutamine also contains a side chain, H₂NC=OCH₂CH₂.⁴ Glutamine, symbolized as Gln or Q, has a molecular formula of C₅H₁₀N₂O₃. The molecular weight is 146.15 g/mol, and the isoelectric point is at 5.65 pH.⁵

Glucagon is a polypeptide containing Glutamine within the compound. The body building formula sold to increase muscle size is usually made up of Glutamine peptides. The ideal product to have for body building would contain Glutamine peptides and glutamine in the free form. Glutamine peptides are more stable and better assimilated by the body.²

Figure 2: Glucagon (plypeptide containing Glutamine)⁶

References:

1.      Lefers, Mark; Glutamine; 2004; [Web] http://groups.molbiosci.northwestern.edu/holmgren/Glossary/Definitions/Def-G/Glutamine.html; Accessed March 23, 2011

2.      BodyBuilding.com; Glutamine; [Web] http://www.bodybuilding.com/store/glutamine.html; Accessed March 23, 2011

3.      Glutamine; 2011; [Web] http://en.wikipedia.org/wiki/Glutamine; Accessed March 23, 2011

4.      Parrill, Abby; Amino Acid Structures; 1997 [Web] http://www.cem.msu.edu/~cem252/sp97/ch24/ch24aa.html; Accessed March 23, 2011

5.      Burkhard, Kirste; Glutamine; 1998; [Web] http://www.chemie.fu-berlin.de/chemistry/bio/aminoacid/glutamin_en.html; Accessed March 23, 2010

6.      Glucagon; 2008; [Web] http://www.lookchem.com/cas-107/107444-51-9.html; Accessed March 23, 2011

Peer-Reviewed Journal with EAS reaction

Resol and novolac are two types of phenolic resins; they are widely used in industry because of their chemical resistance, electrical insulation, and dimensional  stability. Phenolic resin-bonded textile felts can be considered to be fiber-reinforced plastic with high levels of fibers; these fibers are derived from textile scraps recycled from the textile industry. Due to the increase of phenol cost, researchers have been working to partially substitute this monomer by natural polymers that present similiar structure close to that of phenolic resin.

The best possible substitutes of phenol based on cost and availabilty are lignosulfonates, which are obtained from the sulphite process. The ammonium lignosulfonate is the best canidate to substitute phenol, because final properties of phenolic resins are better. Lignosulfonates are not very reactive with phenol and formaldehyde, so it is usual to modify their structure by methyloletion and phenolation. Although phenolation is more expensive.

The reaction mechnism associated with the formulation of lignin-novolac is explained in the following text. The alpha-carbon of the lateral chain of the phenyl-propane units is occupied by the sulfonate group. Lignosulfonates may be reacting by itself or with the phenol adding to the Beta-carbon of the lateral chain. The first step consists of the condensation between lignin fragments and the phenol present with formaldehyde. In the second step, vacuum distillation is employed to adjust the content of free phenol in accordance with the required specifications for textile felt applications. The addition of a curing agent (HMTA) with methylene groups is also necessary for the crosslinking. (1)

On page 3/14, of the following link is Figure 2: Mechanism of lignin-novolac resins synthesis substituted with lignosulfonates. Since this peer-reviewed journal is protected, I could not copy the reaction scheme onto my blog. My apologies.

http://www.ncsu.edu/bioresources/BioRes_02/BioRes_02_2_270_283_Perez_RAOE_Novolac_Resin_Lignosulfonate.pdf

References:
1. Characterization of a Novolac; Jaun Manuel Perez; Bioresources; http://www.ncsu.edu/bioresources/BioRes_02/BioRes_02_2_270_283_Perez_RAOE_Novolac_Resin_Lignosulfonate.pdf; Web; (2007)