Alanyl glutamine is a dipeptide, a conditionally essential amino acid with a dietary supplement function, formed from L-alanyl and L-glutamine residues, which can play a role as a metabolite and is an important energy substance for immune cells (1). In the human body, the amino acids released from the breakdown of this dipeptide are stored and subsequently metabolised.

Industrially it occurs as a white, stable, odourless, hygroscopic powder, soluble in water, in glacial acetic acid, almost insoluble or insoluble in methanol or ethanol.

What it is used for and where

It can be used for parenteral nutrition support.

Medical and Pharmaceutical

The role of Alanyl glutamine in the efficacy and treatment reliability of nutritional support therapy for patients with sepsis, an infection of the bloodstream that causes lower blood pressure, fever and increased heart rate, was investigated. Results have shown that Alanyl glutamine can provide nutritional support for lymphocytes and maintain antioxidant reserves in body tissues (2). It has also been shown that dietary glutamine supplementation improves intestinal function (3) by protecting the function of the intestinal barrier (4) and can improve weight gain in children at risk of environmental enteropathy in the short term (5).

Alanyl glutamine also has an anti-inflammatory action that improves wound healing. This study considers that Alanyl glutamine administered in the form of a dipeptide or in the form of free glutamine could promote neovascularisation and improve the survival of skin flaps in laboratory animals (6). This other study found a positive metabolic effect of Alanyl glutamine on skin burns (7).

Alanyl glutamine studies

Typical commercial product characteristics  Alanyl glutamine

• Molecular Formula  C₈H₁₅N₃O₄
• Molecular Weight  217.22
• CAS  39537-23-0
• UNII    U5JDO2770Z
• EC Number   609-717-9
• DSSTox Substance ID  DTXSID20192658
• IUPAC  (2S)-5-amino-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid
• InChI=1S/C8H15N3O4/c1-4(9)7(13)11-5(8(14)15)2-3-6(10)12/h4-5H,2-3,9H2,1H3,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1 
• InChl Key      HJCMDXDYPOUFDY-WHFBIAKZSA-N
• SMILES   CC(C(=O)NC(CCC(=O)N)C(=O)O)N
• MDL number  MFCD00133046
• PubChem Substance ID    24891211
• ChEBI  73788
• FEMA   4712  
• JECFA    2121    
• NCI   C127908

Synonyms

• l-Alanyl-l-glutamine
• Glutamine-S
• H-Ala-Gln-OH
• alanylglutamine
• Ala-gln

References_______________________________________________________________________

(1) Lacey JM, Wilmore DW. Is glutamine a conditionally essential amino acid? Nutr Rev. 1990 Aug;48(8):297-309. doi: 10.1111/j.1753-4887.1990.tb02967.x. 

(2) Su X, Li Y, Zhang Y, Han S. Efficacy of alanyl glutamine in nutritional support therapy for patients with sepsis: A protocol for systematic review and meta-analysis. Medicine (Baltimore). 2021 Mar 19;100(11):e24861. doi: 10.1097/MD.0000000000024861.

(3) Soares AD, Costa KA, Wanner SP, Santos RG, Fernandes SO, Martins FS, Nicoli JR, Coimbra CC, Cardoso VN. Dietary glutamine prevents the loss of intestinal barrier function and attenuates the increase in core body temperature induced by acute heat exposure. Br J Nutr. 2014 Nov 28;112(10):1601-10. doi: 10.1017/S0007114514002608.

(4) Freitas AKL, Silva MTB, Silva CMS, Prata MMG, Rodrigues FAP, Siqueira RJB, Lima AAM, Santos AA, Havt A. Alanyl-glutamine protects the intestinal barrier function in trained rats against the impact of acute exhaustive exercise. Braz J Med Biol Res. 2020 Apr 17;53(5):e9211. doi: 10.1590/1414-431X20209211.

(5) Moore SR, Quinn LA, Maier EA, Guedes MM, Quetz JS, Perry M, Ramprasad C, Lanzarini Lopes GML, Mayneris-Perxachs J, Swann J, Soares AM, Filho JQ, Junior FS, Havt A, Lima NL, Guerrant RL, Lima AAM. Intervention and Mechanisms of Alanyl-glutamine for Inflammation, Nutrition, and Enteropathy: A Randomized Controlled Trial. J Pediatr Gastroenterol Nutr. 2020 Sep;71(3):393-400. doi: 10.1097/MPG.0000000000002834. 

(6) Karimipour M, Hassanzadeh M, Zirak Javanmard M, Farjah G. Oral administration of alanyl-glutamine and glutamine improve random pattern dorsal skin flap survival in rats. Iran J Basic Med Sci. 2018 Aug;21(8):842-847. doi: 10.22038/IJBMS.2018.29629.7153.

(7) Barbosa RC, Guimarães SB, de Vasconcelos PR, Chaves CR, de Vasconcelos PR. Metabolic effects of l-alanyl-glutamine in burned rats. Burns. 2006 Sep;32(6):721-7. doi: 10.1016/j.burns.2005.12.014.