Acetyl-L-glutamic acid (BAT-003849)
* For research use only

A substrate for acetylglutamate kinase. An inhibitor of N-acetyl-L-glutamate synthetase.

Category
Inhibitors containing Unusual Amino Acids
Catalog number
BAT-003849
CAS number
1188-37-0
Molecular Formula
C7H11NO5
Molecular Weight
189.17
Acetyl-L-glutamic acid
Synonyms
Ac-L-Glu-OH
Appearance
White or off-white crystalline powder
Purity
98-102% (Assay)
Density
1.4119 (rough estimate)
Melting Point
199-201ºC
Boiling Point
324.41°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChI Key
RFMMMVDNIPUKGG-YFKPBYRVSA-N
Canonical SMILES
CC(=O)NC(CCC(=O)O)C(=O)O
1.Fourier transform IR study of aggregational behavior of N-acetyl-L- and N-butyloxycarbonyl-L-glutamic acid oligomeric benzyl esters in dioxane and benzene: beta-turn --> antiparallel beta-sheet transition.
Okabayashi H1, Ishida M, Tamaoki H, Masuda H, O'Connor CJ. Biopolymers. 2002 Oct 15;65(2):129-41.
Oligomeric N-acetyl-L-glutamic acid benzyl esters (AN(p)Z) with exact residue numbers (N(p) = 2, 3, 4, and 5) and N-butyloxycarbonyl-L-glutamic acid benzyl esters (BOCN(p)Z) with exact residue numbers (N(p) = 4, 5, 6, and 8) are synthesized by a stepwise procedure in a liquid phase. The aggregational behavior of these oligomeric molecules in dioxane and benzene is examined by Fourier transform IR spectra. In particular, the concentration dependence of the IR spectra for the AN(p)Z solutions with N(p) values of 4 (A4Z) and 5 (A5Z) shows that the predominant antiparallel beta-sheet structure is stabilized above the critical aggregation concentration (cac), while other conformations including beta-turns may coexist below the cac. This fact provides evidence that aggregation induces the conformational transition from other conformers (probably beta-turns) to an antiparallel beta-sheet form. The IR results for the A3Z and A2Z solutions indicate that specific conformers (beta-turns), which are different from the beta-sheet structure, may be preferentially stabilized upon aggregation.
2.N-acetyl-L-glutamic acid.
Dobson AJ1, Gerkin RE. Acta Crystallogr C. 1997 Jan 15;53 ( Pt 1):73-6.
In the structure of N-acetyl-L-glutamic acid, C7H11NO5, each molecule is directly hydrogen bonded to four others by a total of six hydrogen bonds. Two carboxylic O atoms and the N atom are donors, while all three acceptors are O atoms. There is also an intramolecular hydrogen bond with the N atom as donor and a carboxylic O atom as acceptor. The carboxyl O and H atoms are ordered. The conformation of the carbon chain with respect to the C3-C4 bond is trans as in L-glutamic acid hydrochloride, rather than gauche as in the beta form of L-glutamic acid.
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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