(R)-homobenzyl-β-alanine
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(R)-homobenzyl-β-alanine

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Category
β−Amino Acids
Catalog number
BAT-014147
CAS number
147228-37-3
Molecular Formula
C11H15NO2
Molecular Weight
193.24
(R)-homobenzyl-β-alanine
IUPAC Name
(3R)-3-amino-5-phenylpentanoic acid
Synonyms
D-β-Nva(5-phenyl)-OH; (R)-3-Amino-5-phenylpentanoic acid; (R)-3-Amino-5-phenyl-pentanoic acid
Related CAS
331846-98-1 (hydrochloride)
Appearance
White to Off-white Powder
Purity
≥ 98%
Density
1.133±0.06 g/cm3(Predicted)
Melting Point
150-156°C
Boiling Point
368.2±42.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H15NO2/c12-10(8-11(13)14)7-6-9-4-2-1-3-5-9/h1-5,10H,6-8,12H2,(H,13,14)/t10-/m1/s1
InChI Key
CJJYCYZKUNRKFP-SNVBAGLBSA-N
Canonical SMILES
C1=CC=C(C=C1)CCC(CC(=O)O)N

(R)-homobenzyl-β-alanine, a chiral amino acid derivative with profound implications for bioscience and the pharmaceutical industry, offers a plethora of applications. Here are the key applications showcased with a high degree of perplexity and burstiness:

Chiral Synthesis: Serving as a pivotal chiral building block, (R)-homobenzyl-β-alanine plays a pivotal role in synthesizing enantiomerically pure pharmaceutical compounds. Its unique stereochemistry enables seamless integration into intricate molecules with desired chiral configurations. This feature holds paramount importance in drug development, where the chirality of a compound exerts a significant impact on both its efficacy and safety.

Peptide Synthesis: Positioned at the forefront of peptide synthesis, this chiral amino acid derivative facilitates the creation of peptides boasting precise functional properties. By incorporating (R)-homobenzyl-β-alanine into peptide chains, researchers can craft peptides endowed with distinctive biological activities and stability profiles. These specialized peptides find utility in diverse realms such as drug development, biochemical research, and therapeutic applications.

Ligand Design: (R)-homobenzyl-β-alanine emerges as a key player in the realm of designing novel ligands tailored for receptors and enzymes. Its specific structural attributes render it a valuable component in the construction of molecules capable of selectively binding to biological targets. This application assumes critical significance in the development of novel drugs and gaining comprehensive insights into intricate receptor-ligand interactions.

Bioconjugation: Positioned at the intersection of bioactive molecules and substrates, (R)-homobenzyl-β-alanine proves to be a versatile asset in bioconjugation applications. By facilitating the attachment of bioactive molecules to a diverse array of substrates, it amplifies the delivery and efficacy of therapeutic agents, imaging probes, and other bioactive compounds in biological systems. This capability holds particular promise in enhancing targeted drug delivery and diagnostic applications, heralding advancements in precision medicine.

1.beta-Lactam derivatives as enzyme inhibitors: 1-peptidyl derivatives of 4-phenylazetidin-2-one as inhibitors of elastase and papain.
Achilles K1, Schirmeister T, Otto HH. Arch Pharm (Weinheim). 2000 Aug;333(8):243-53.
N-Peptidyl substituted azetidin-2-ones were synthesized and evaluated as inhibitors of the serine protease elastase, and the cysteine protease papain. All compounds were synthesized from 4-phenylazetidin-2-one, either from the racemate or from the pure enantiomers. The (S)-enantiomer was prepared by enantioselective synthesis from (S)-beta-phenyl-beta-alanine, while the (R)-enantiomer was obtained by enzymatic resolution with alpha-chymotrypsin. N-Alkylation with bromoacetates introduced a spacer group which, after hydrolysis to the free acid, was acylated with amino acid esters or di- or tripeptide esters. The enzymatic assays proved some derivatives to be effective inhibitors of PPE and/or papain. N-BOC protected amino acid derivatives without a spacer group inhibited PPE reversibly, while derivatives with spacer group showed either weak or no inhibitory properties. On the other hand, papain was inactivated irreversibly by ethyl (RS)-2-oxo-4-phenylazetidin-1-acetate.
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