D-Alanine
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D-Alanine

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Alanine (abbreviated as Ala or A) is a non-polar α-amino acid, with the formula CH3CH(NH2)COOH. The L-isomer (left-handed) of alanine is one of the 20 amino acids encoded by the human genetic code. Its genetic codons are GCU, GCC, GCA, and GCG. L-Alanine is second only to leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins.The right-handed form, D-Alanine occurs in bacterial cell walls and in some peptide antibiotics.

Category
D-Amino Acids
Catalog number
BAT-014292
CAS number
338-69-2
Molecular Formula
C3H7NO2
Molecular Weight
89.09
D-Alanine
IUPAC Name
(2R)-2-aminopropanoic acid
Synonyms
D-Ala-OH; D-alpha-Aminopropionic acid
Appearance
White to Off-white Crystalline Powder
Purity
>98%
Density
1.161g/cm3
Melting Point
291 ℃
Storage
Store at RT
Application
amino acid
InChI
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
InChI Key
QNAYBMKLOCPYGJ-UWTATZPHSA-N
Canonical SMILES
CC(C(=O)O)N
1.Inoculation of sugarcane with Pantoea sp. increases amino acid contents in shoot tissues; serine, alanine, glutamine and asparagine permit concomitantly ammonium excretion and nitrogenase activity of the bacterium.
Loiret FG;Grimm B;Hajirezaei MR;Kleiner D;Ortega E J Plant Physiol. 2009 Jul 15;166(11):1152-61. doi: 10.1016/j.jplph.2009.01.002. Epub 2009 Feb 11.
Pantoea sp. is an endophytic nitrogen-fixing bacterium isolated from sugarcane tissues. The aim of the present study was to determine the contents of amino acids in sugarcane as a result of inoculation of nodes and nodal roots with Pantoea sp. strain 9C and to evaluate the effects of amino acids on growth, nitrogenase activity and ammonium excretion of the bacterium. Content of almost all amino acids increased in 30-day-old plantlets by root inoculation. The most abundant amino acids in shoot tissues were asparagine and proline, and those in nodal roots were asparagine, proline, aspartic acid, glutamic acid and serine. The bacterium was able to grow on all tested amino acids except histidine, isoleucine and leucine. Nitrogenase Pantoea sp. was partially inhibited by 1, 2 or 5mmolL(-1) and completely inhibited by 10mmolL(-1) of NH(4)(+) in the media. Pantoea sp. showed nitrogenase activity in 5mmolL(-1) of serine, asparagine, threonine, alanine, proline, tyrosine, valine, methionine, lysine, phenylalanine, cysteine, tryptophan, citrulline and ornithine. Pantoea sp. did not excrete ammonium when it grew in vivo conditions favoring nitrogen fixation; however, ammonium was detected in the supernatant when 5mmolL(-1) asparagine, aspartic acid, alanine, serine or glutamine was added to the medium.
2.DFT Studies of NH-Cl Hydrogen Bond of Amino Acid Hydrochloride Salts in Ion Channels.
Moridi M;Shekarsaraei S;Hadipour NL Acta Chim Slov. 2016;63(2):241-50.
Quantum chemical calculations were made, to study NH-Cl hydrogen bonds of two amino acid hydrochloride salts called alanine and threonine. The Nuclear Magnetic Resonance and Nuclear Quadrupole Resonance parameters for nitrogen and chlorine were calculated via four functionals such as, B3LYP, M062X, M06L, and CAM-B3LYP and by applying the 6-311++G(d,p) basis set. One of the functionals produced more accurate results. Geometry optimization was performed using the M062X/6-31++G(d,p) method, and Natural Bond Orbitals analysis was performed by applying the M062X/6-311++G(d,p) level. This study examined Nuclear Magnetic Resonance and Nuclear Quadrupole Resonance parameters with changes in structure from monomer to pentamer and investigated correlations between Natural Bond Orbitals parameters and Nuclear Magnetic Resonance or Nuclear Quadrupole Resonance parameters. The Natural Bond Orbitals parameters were used to investigate changes in structural parameters along with crystal development.
3.Design and synthesis of novel HDAC8 inhibitory 2,5-disubstituted-1,3,4-oxadiazoles containing glycine and alanine hybrids with anti cancer activity.
Pidugu VR;Yarla NS;Pedada SR;Kalle AM;Satya AK Bioorg Med Chem. 2016 Nov 1;24(21):5611-5617. doi: 10.1016/j.bmc.2016.09.022. Epub 2016 Sep 12.
Oxadiazole is a heterocyclic compound containing an oxygen atom and two nitrogen atoms in a five-membered ring. Of the four oxadiazoles known, 1,3,4-oxadiazole has become an important structural motif for the development of new drugs and the compounds containing 1,3,4-oxadiazole cores have a broad spectrum of biological activity. Herein, we describe the design, synthesis and biological evaluation of a series of novel 2,5-disubstituted 1,3,4-oxadiazoles (10a-10j) as class I histone deacetylase (HDAC) inhibitors. The compounds were designed and evaluated for HDAC8 selectivity using in silico docking software (Glide) and the top 10 compounds with high dock score and obeying Lipinski's rule were synthesized organically. Further the biological HDAC inhibitory and selectivity assays and anti-proliferative assays were carried out. In in silico and in vitro studies, all compounds (10a-10j) showed significant HDAC inhibition and exhibited HDAC8 selectivity. Among all tested compounds, 10b showed substantial HDAC8 inhibitory activity and better anticancer activity which is comparable to the positive control, a FDA approved drug, vorinostat (SAHA). Structural activity relation is discussed with various substitutions in the benzene ring connected on 1,3,4-oxadizole and glycine/alanine.
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