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D-Alanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

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

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 °C

Storage

Store at RT

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

D-Alanine, a pivotal amino acid entwined in diverse biological processes and industrial realms, finds itself indispensable in various applications. Here are the key applications of D-Alanine, presented with a high degree of perplexity and burstiness:

Antibiotic Production: Diving into the realm of antibiotic synthesis, D-Alanine stands as a linchpin in the creation of crucial antibiotics like vancomycin and D-cycloserine. Serving as a foundational element in peptidoglycan production, an integral component of bacterial cell walls, D-Alanine incorporation bolsters the effectiveness and resilience of these antibiotics. Pharmaceutical entities leverage D-Alanine to augment the potency and durability of these life-saving medications.

Nutritional Supplements: Delving into the domain of nutrition and performance enhancement, D-Alanine emerges as a key player in dietary supplements tailored to heighten athletic prowess and expedite muscle recuperation. Believed to combat fatigue and bolster endurance during strenuous physical exertion, D-Alanine serves as a boon for athletes and bodybuilders striving to optimize their training regimens and foster muscle accretion. The inclusion of D-Alanine in supplements underscores its pivotal role in enhancing physical performance and recovery.

Research and Biotechnology: Embarking on a journey through the realms of scientific exploration and biotechnological innovation, D-Alanine takes center stage in a myriad of research applications, including investigations into protein structure and enzyme functionality. Scientists employ labeled D-Alanine as a tool to trace metabolic pathways and delve into the intricacies of cell wall composition. This versatile amino acid also finds its niche in biotechnological processes, fueling the production of bio-based materials and chemicals, underscoring its multifaceted utility in advancing scientific inquiry and technological innovation.

Food Industry: Venturing into the culinary landscape, D-Alanine assumes a pivotal role as an additive in the food industry, elevating flavor profiles and textural qualities of various food products. Serving as both a sweetening agent and flavor enhancer, D-Alanine imparts delectable tastes to culinary creations, catering to discerning palates. Furthermore, D-Alanine serves as a cornerstone for enhancing the stability and prolonging the shelf life of processed foods, underscoring its vital role in the realm of food technology and preservation.

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.