L-Glutamine

This was one of two molecules this week
September 25, 2017
We two amino acids can make a whale of a difference.
What molecules are we?
Image of L-Glutamine 3D Image of L-Glutamine
Figure 1: L-Glutamine
Image of L-Glutamine 3D Image of L-Glutamine
Figure 2: L-Arginine

L-Glutamine and L-arginine are classified as semi-essential or conditionally essential amino acids, which means that the human body can synthesize them under some health conditions but not others. Both are abundant in many foods.

Neither D-glutamine nor D-arginine is common in nature, so the L-amino acids are usually referred to without prefixes. In 1883, German chemists Ernst. Schulze and E. Bosshard isolated L-glutamine from the juice of sugarbeets. It is the most common amino acid in human blood and a key component of proteins.

In 1886, Schulze was also the first to isolate L-arginine, in this case from lupin seedlings. It is also an important amino acid in protein biosynthesis.

It turns out that a difference in occurrence between these two amino acids makes a huge difference in huge animals. This year, while examining the melanocortin system* of cetaceans, Roger D. Cone at the University of Michigan (Ann Arbor) and colleagues discovered that the two suborders of the sea mammals have different components at position 156 in the melanocortin-4 receptor. Glutamine is at this position in baleen whales, whereas toothed whales and dolphins contain arginine instead.

Cone’s group found that arginine in the receptor suppresses the beasts’ appetites relative to the glutamine-containing receptor. They believe that this difference contributes to the much larger sizes of baleen whales.

*The melanocortin system is an important regulator of metabolism, food intake, and fat storage.

L-Glutamine Fast Facts

CAS Reg. No. 56-85-9
Molar mass 146.14 g/mol
Formula C5H10N2O3
Appearance White crystals or powder 
Melting point 185 ºC (dec.)
Water solubility 25 g/L

L-Arginine Fast Facts

CAS Reg. No. 74-79-3
Molar mass 174.20 g/mol
Formula C6H14N4O2
Appearance White crystals or powder
Melting point 244 ºC (dec.)
Water solubility 15 g/L
Chemical Abstract Service - a division of ACS

Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.

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