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A0550

Sigma-Aldrich

Ala-Gln

≥98% (HPLC)

Synonym(s):

Alanyl-glutamine, Glutamine-S

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About This Item

Empirical Formula (Hill Notation):
C8H15N3O4
CAS Number:
39537-23-0
Molecular Weight:
217.22
MDL number:
MFCD00133046
UNSPSC Code:
12352209
PubChem Substance ID:
24890433
NACRES:
NA.26

product name

Ala-Gln, ≥98% (HPLC)

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

white to off-white

SMILES string

NC(CC[C@H](NC([C@@H](N)C)=O)C(O)=O)=O

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

InChI key

HJCMDXDYPOUFDY-WHFBIAKZSA-N

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Application

L-Glutamine is an essential supplement for cell culture. The free amino acid L-glutamine is unstable and degrades to pyroglutamate. Alanyl-L-glutamine (Ala-Gln) and Gylcyl-L-glutamine (Gly-Gln) are used in cell culture as alternative delivery forms of stabilized L-glutamine. The primary advantage of using L-alanylglutamine in place of L-glutamine is that it reduces the level of ammonia generated during cell culture.

Biochem/physiol Actions

Alanyl-glutamine is a widely used alternative supplement to L-glutamine in the production of biopharmaceuticals. Alanyl-glutamine also acts as an antioxidant (peroxide) and anti-apoptosis (LPS-induced) factor. Ala-Gln has been used in studies on injury and sepsis, and on the effects of irradiation on leucine and protein metabolism in vivo. Ala-Gln has been utilized to investigate polymorphonuclear leucocyte and myeloperoxidase activity in vitro.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G Biolo et al.
Nutrition (Burbank, Los Angeles County, Calif.), 13(9 Suppl), 52S-57S (1997-09-18)
The metabolic response to trauma and sepsis involves an increased loss of body proteins. Specific sites of changes of protein and amino acid metabolism have been identified. In skeletal muscle, the rate of proteolysis is accelerated greatly. The rate of
A Christie et al.
Biotechnology and bioengineering, 64(3), 298-309 (1999-07-09)
Although glutamine is a major carbon source for mammalian cells in culture, its chemical decomposition or cellular metabolism leads to an undesirable excess of ammonia. This limits the shelf-life of glutamine-supplemented media and may reduce the cell yield under certain
John D Biggers et al.
Reproductive biomedicine online, 9(1), 59-69 (2004-07-20)
A comparison of the effects of replacing L -glutamine with either glycyl-L-glutamine or alanyl-L-glutamine in a KSOM-type medium on the development of mouse preimplantation embryos in vitro has been made. Alanyl-L-glutamine has no significant effect on the rates of blastocyst
J Mühling et al.
Amino acids, 22(1), 39-53 (2002-05-25)
The objective of this study was to determine the effects of arginine, L-alanyl-L-glutamine (Ala-Gln) or taurine on polymorphonuclear leucocyte (PMN) free amino acid profiles, superoxide anion (O2-) generation, hydrogen peroxide (H2O2) formation and released myeloperoxidase activity (MPO). Arginine led to
M Holecek et al.
Amino acids, 22(1), 95-108 (2002-05-25)
The mechanism by which glutamine produces a favorable effect in the treatment of sepsis, injury, burns and abdominal irradiation is not completely understood. The main aim of this study was to evaluate the effect of alanyl-glutamine (AlaGln) administration on the
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