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3-(3'-Pyridyl)-DL-alanine

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

Category

DL-Amino Acids

Catalog number

BAT-007807

CAS number

17470-24-5

Molecular Formula

C8H10N2O2

Molecular Weight

166.18

IUPAC Name

2-amino-3-pyridin-3-ylpropanoic acid

Synonyms

DL-Ala(3'-pyridyl)-OH; 2-Amino-3-pyridin-3-yl-propionic acid; H-DL-3-PAL-OH; 3-(3-Pyridyl)-DL-alanine; BETA-(3-PYRIDYL)-DL-ALANINE; 3-Pyridinepropanoic acid, alpha-amino-; H-BETA-(3-PYRIDYL)-ALA-OH; 3-Pyridin-3-yl-D-alanine; H-3-Pal-OH; (S)-2-Amino-3-pyridin-3-yl-propionic acid; 3-(3-pyridinyl)alanine

Appearance

White powder

Purity

≥ 99% (HPLC)

Density

1.271±0.06 g/cm3 (Predicted)

Melting Point

268 °C

Boiling Point

344.4±32.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C8H10N2O2/c9-7(8(11)12)4-6-2-1-3-10-5-6/h1-3,5,7H,4,9H2,(H,11,12)

InChI Key

DFZVZEMNPGABKO-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CN=C1)CC(C(=O)O)N

3-(3'-Pyridyl)-DL-alanine, a synthetic amino acid analog, holds diverse applications in biochemical research and pharmacology. Here are the key applications, presented with high perplexity and burstiness:

Neuropharmacology: Integral to the study of neurotransmitter systems in the brain, 3-(3'-Pyridyl)-DL-alanine serves as a pivotal tool for investigating the intricate mechanisms of neurotransmitter release and uptake. By integrating this compound into neuronal assays, researchers can delve into its impacts on vital neurotransmitter systems like dopamine or serotonin, shedding light on brain function and disorders. This compound plays a crucial role in shaping innovative treatments for afflictions ranging from depression to schizophrenia and Parkinson's disease.

Enzyme Inhibition Studies: A cornerstone in biochemical research, this compound plays a crucial role in exploring enzyme kinetics and inhibition mechanisms. By acting as both a substrate and an inhibitor, it enables scientists to probe the active sites of enzymes and their catalytic pathways, offering crucial insights into the development of enzyme inhibitors as potential therapeutics for a myriad of diseases spanning from cancer to infectious ailments.

Radiolabeling: In the realm of molecular imaging and diagnostics, 3-(3'-Pyridyl)-DL-alanine emerges as a pivotal player in radiolabeling studies. Once labeled with a radioactive isotope, this compound becomes a valuable tracer in biological systems, facilitating the study of biodistribution, metabolism, and cellular uptake. This application holds significant weight in both preclinical and clinical research realms, aiding in the imaging of tumors, monitoring metabolic processes, and investigating disease progression with precision.

Protein Structure Analysis: Delving into the nuances of protein dynamics, researchers harness 3-(3'-Pyridyl)-DL-alanine in protein structure-function studies to decipher the conformational changes and interactions within proteins. By incorporating this analog into protein sequences, scientists embark on a journey to unravel its effects on protein folding and stability, using techniques like NMR spectroscopy or X-ray crystallography. This profound understanding of protein dynamics not only aids in unraveling fundamental biological mechanisms but also in crafting novel proteins endowed with desired properties.

1. General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid

M Sharma, C R Petrie 3rd, W Korytnyk Carbohydr Res. 1988 Apr 1;175(1):25-34. doi: 10.1016/0008-6215(88)80153-8.

Methyl 5-acetamido-3,5-dideoxy-2-O-methyl-D-glycero-D-galacto-2-nonulopyrano sate was converted into the 9-O-trityl derivative and the remaining hydroxyl groups were protected as benzyl ethers. Removal of the trityl group, followed by treatment with diethylaminosulfur trifluoride gave the 9-deoxy-9-fluoro derivative, and deprotection N-acetyl-9-deoxy-9-fluoroneuraminic acid (8). In another procedure, coupling of 2-acetamido-2,6-dideoxy-6-fluoro-D-glucopyranose with potassium di(tert-butyl) oxaloacetate, followed by hydrolysis and decarboxylation gave 8. Some of the derivatives were active as inhibitors of growth of mouse mammary adenocarcinoma (TA3) and L1210 cells in culture.

2. Synthesis of heparin fragments. A chemical synthesis of the pentasaccharide O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-4 )-O-(beta-D-glucopyranosyluronic acid)-(1-4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glu copyranosyl)-(1-4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1-4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose decasodium salt, a heparin fragment having high affinity for antithrombin III

M Petitou, P Duchaussoy, I Lederman, J Choay, P Sinaÿ, J C Jacquinet, G Torri Carbohydr Res. 1986 Mar 15;147(2):221-36. doi: 10.1016/s0008-6215(00)90633-5.

Known allyl 4,6-O-benzylidene-alpha-D-glucopyranoside was first converted into methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-alpha-D-glucopyranosid)-uronate. Acid hydrolysis, followed by treatment with (bromomethylene)dimethyl-ammonium bromide, gave methyl (2,3-di-O-benzyl-4-O-chloroacetyl-alpha-D-glucopyranosyl bromide)uronate. Condensation of this bromide with 3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-beta-D-glucopyranosyluronate)-bet a-D-glucopyranose. Acetolysis, followed by treatment with titanium tetrabromide, then gave 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-beta-D-glucopyranosyluronate)-alp ha-D-glucopyranosyl bromide. Condensation of this bromide with benzyl 6-O-acetyl-3-O-benzyl-2-benzyloxy- carbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-alpha-L- idopyranosyluronate)-alpha-D-glucopyranoside provided benzyl O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-beta-D-glucopyranosyluronate)-(1- ---4)-O-(3,6-di-O-acetyl- -2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(methyl 2-O-acetyl-3-O-benzyl-alpha-L-idopyranosyluronate)-(1----4)-6-O-ac etyl-3-O- acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-gluc opyranoside. O-Dechloroacetylation followed by condensation with 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide provided benzyl O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)- (1----4)-O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)- O-(3,6-di-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(m ethyl 2-O-acetyl-3-O-benzyl-alpha-L-idopyranosyluronate)-(1----4)-6-O-ac etyl-3-O- benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside in 70% yield. O-Deacetylation followed by re-esterification, O-sulfation, saponification, catalytic hydrogenolysis, and N-sulfation gave the decasodium salt of O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D- glucopyranosyl)-(1----4)-O-(beta-D-glucopyranosyluronic acid)-(1----4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-gl ucopyranosyl)-(1----4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic+ ++ acid)-(1----4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose. This synthetic pentasaccharide binds to antithrombin III with an association constant similar to that of high-affinity heparin and elicits a potent anti-factor Xa activity in plasma.

3. Synthesis and reactions of O-acetylated benzyl alpha-glycosides of 6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-N-acetylmuramoyl-L- alanyl-D-isoglutamine esters: the base-catalysed isoglutamine in equilibrium glutamine rearrangement in peptidoglycan-related structures

D Keglević, A E Derome Carbohydr Res. 1989 Feb 15;186(1):63-75. doi: 10.1016/0008-6215(89)84005-4.

Condensation of benzyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2- deoxy-3-O-[(R)-1-carboxyethyl]-alpha-D-glucopyranoside (2) and its 4-acetate (4) with L-alanyl-D-isoglutamine benzyl ester via the mixed anhydride method yielded N-(2-O-[benzyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D- glucopyranosyl)-2,3-dideoxy-alpha-D-glucopyranosid-3-yl]-(R)-lacto yl)-L- alanyl-D-isoglutamine benzyl ester (5) and its 4-acetate (6), respectively. Condensation by the dicyclohexylcarbodi-imide-N-hydroxysuccinimide method converted 2 into benzyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl- 2-deoxy-beta-D-glucopyranosyl)-3-O-[(R)-1-carboxyethyl]-2-deoxy-alpha-D- glucopyranoside 1',4-lactone (7). In the presence of activating agents, 7 underwent aminolysis with the dipeptide ester to give 5. Zemplén O-deacetylation of 5 and 6 led to transesterification and alpha----gamma transamidation of the isoglutaminyl residue to give N-(2-O-[benzyl 2-acetamido-6-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-2,3-dideoxy-alpha-D-glucopyr anosid-3- yl]-(R)-lactoyl)-L-alanyl-D-isoglutamine methyl ester (8) and -glutamine methyl ester (9). Treatment of 6 with MgO-methanol caused deacetylation at the GlcNAc residue to give a mixture of N-(2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2- deoxy-beta-D-glucopyranosyl)-4-O-acetyl-2,3-dideoxy-alpha-D-glucopyra nosid-3- yl]-(R)-lactoyl)-L-alanyl-D-isoglutamine methyl ester (11) and -glutamine methyl ester (12). Benzyl or methyl ester-protection of peptidoglycan-related structures is not compatible with any of the reactions requiring alkaline media. Condensation of 2 with L-alanyl-D-isoglutamine tert-butyl ester gave N-(2-O-[benzyl 2-acetamido- 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-2,3-d ideoxy- alpha-D-glucopyranosid-3-yl]-(R)-lactoyl-L-alanyl-D-isoglutamine tert-butyl ester (16), deacetylation of which, under Zemplén conditions, proceeded without side-reactions to afford N-(2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-2,3-dideoxy-alpha-D-glucopyranosid-3-yl]-(R)-la cotyl)-L- alanyl-D-isoglutamine tert-butyl ester (17).