H-D-Ala(3-pyridyl)-OH
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H-D-Ala(3-pyridyl)-OH

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A reagent used in the synthesis of selective ligands derived from somatostatin antagonists.

Category
D-Amino Acids
Catalog number
BAT-000863
CAS number
70702-47-5
Molecular Formula
C8H10N2O2
Molecular Weight
166.18
H-D-Ala(3-pyridyl)-OH
IUPAC Name
(2R)-2-amino-3-pyridin-3-ylpropanoic acid
Synonyms
3-(3-Pyridyl)-D-alanine; (R)-2-Amino-3-(pyridin-3-yl)propanoic acid
Purity
95%
Density
1.271 g/cm3
Boiling Point
370.4°C at 760 mmHg
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)/t7-/m1/s1
InChI Key
DFZVZEMNPGABKO-SSDOTTSWSA-N
Canonical SMILES
C1=CC(=CN=C1)CC(C(=O)O)N

H-D-Ala(3-pyridyl)-OH, a synthetic amino acid derivative, finds diverse applications in bioscience research. Explore its key applications presented with elevated perplexity and burstiness:

Peptide Synthesis: Acting as a fundamental element in peptide and protein synthesis, H-D-Ala(3-pyridyl)-OH contributes to the assembly of peptides with tailored functionalities and heightened stability. This facet is pivotal for the innovation of novel therapeutics and biomaterials, forging new paths in the realm of medical research.

Drug Design and Discovery: Spearheading the domain of drug development, H-D-Ala(3-pyridyl)-OH plays a critical role in crafting peptide-based drugs with optimized pharmacokinetic attributes. By integrating this compound into drug design, researchers augment the drug's binding affinity and specificity, ushering in a new era of potent and precisely targeted treatment modalities.

Bioconjugation: A versatile tool in bioconjugation methodologies, H-D-Ala(3-pyridyl)-OH facilitates the labeling and modification of proteins and peptides. The pyridyl group offers a convenient linkage site for coupling with diverse molecules such as fluorescent probes or drugs, enabling the exploration of protein functionality, tracking biological processes, and advancing diagnostic tool development.

Proteomics: Within the realm of proteomics, H-D-Ala(3-pyridyl)-OH serves as a cornerstone for structural and functional protein analysis. By integrating this derivative into protein frameworks, researchers delve into interactions, stability, and folding patterns, shedding light on protein functionalities and their intricate involvement in diverse biological processes.

1.Improved synthesis and resolution of beta-(3-pyridyl)-DL-alpha-alanine.
Folkers K, Kubiak T, Stepinski J. Int J Pept Protein Res. 1984 Sep;24(3):197-200.
beta-Benzamido-alpha-(3-pyridyl)-DL-alpha-alanine hydrochloride was synthesized from 3-pyridinecarboxyaldehyde via the azlactone which was hydrolyzed to the acrylic acid before hydrogenation. The methyl ester was effectively resolved with subtilisin. The optical purity of the D-isomer was established, since the D-isomer was used in synthesis of antagonists of the luteinizing hormone releasing hormone.
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