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3,3-Diphenyl-L-alanine

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

3,3-Diphenyl-L-alanine is used in the making of l-Diphenylalanine Microtubes that functions as a potential drug delivery systems.

Category

L-Amino Acids

Catalog number

BAT-007815

CAS number

149597-92-2

Molecular Formula

C15H15NO2

Molecular Weight

241.29

IUPAC Name

(2S)-2-amino-3,3-diphenylpropanoic acid

Synonyms

L-Ala(3,3-diphenyl)-OH; (S)-2-Amino-3,3-diphenylpropionic acid; L-3,3-Diphenylalanine; L-Phenylalanine, beta-phenyl-; 3,3-Diphenylalanine; beta-Phenylphenylalanine; beta-Phenyl-L-phenylalanine; (2S)-2-amino-3,3-diphenylpropanoic acid

Appearance

White powder

Purity

≥ 99%

Density

1.198±0.06 g/cm3 (Predicted)

Melting Point

234-240 °C

Boiling Point

389.2±30.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C15H15NO2/c16-14(15(17)18)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H,16H2,(H,17,18)/t14-/m0/s1

InChI Key

PECGVEGMRUZOML-AWEZNQCLSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)C(C(=O)O)N

3,3-Diphenyl-L-alanine, a synthetic amino acid derivative, finds diverse applications in bioscience research and industry. Here are the key applications showcased with a high degree of perplexity and burstiness:

Peptide Synthesis: Delving into peptide and protein synthesis, 3,3-Diphenyl-L-alanine emerges as a crucial tool for deciphering their intricate structures and functions. Its unique side chain introduces conformational constraints into peptides, shedding light on protein folding and stability. Moreover, the compound aids in crafting peptides with heightened biological activity or resilience against enzymatic breakdown, expanding the horizons of molecular exploration.

Drug Design: At the forefront of drug discovery, 3,3-Diphenyl-L-alanine plays a pivotal role in shaping the landscape of peptidomimetics. By integrating this compound into therapeutic peptides, researchers enhance the pharmacokinetic properties of drugs, paving the way for the formulation of more potent and durable drug candidates across diverse disease spectra. This advancement heralds a new era of precision medicine and therapeutic efficacy.

Biological Probes: Serving as a molecular probe in biochemical assays, 3,3-Diphenyl-L-alanine unravels the complex world of enzyme activities and interactions. Its distinct structure acts as a valuable asset in deciphering the nuances of enzyme specificity and substrate recognition, offering profound insights into enzymology. This application stands as a cornerstone in the quest for developing targeted enzyme inhibitors and unraveling the mysteries of molecular interactions.

Material Science: In the realm of material science, 3,3-Diphenyl-L-alanine catalyzes the creation of innovative biomaterials boasting desirable characteristics. By integrating this compound into polymer chains, researchers engineer materials with enhanced mechanical strength, thermal stability, and biocompatibility. These advanced materials hold immense promise in diverse fields ranging from medical devices and tissue engineering to intricate drug delivery systems, ushering in a new era of material innovation.

1. Arginine vasopressin and its analogues--the influence of position 2 modification with 3,3-diphenylalanine enantiomers. Highly potent V2 agonists

Anna Kwiatkowska, Dariusz Sobolewski, Adam Prahl, Lenka Borovicková, Jirina Slaninová, Bernard Lammek Eur J Med Chem. 2009 Jul;44(7):2862-67. doi: 10.1016/j.ejmech.2008.12.010.

Eleven new analogues of arginine vasopressin (AVP) modified in position 2 by 3,3-diphenyl-L-alanine or its D-enantiomer (Dip or D-Dip) were synthesized and pharmacologically evaluated for their pressor, antidiuretic and in vitro uterotonic activities. Both the Dip and D-Dip modifications at position 2 of AVP are sufficient to completely change the pharmacological profile of the peptides. They preserve or increase antidiuretic activity, cause its prolongation, transform uterotonic property in antagonistic one and cancel the effect on blood pressure. Four of the new peptides ([Mpa1,D-Dip2]AVP, [Mpa1,D-Dip2,Val4]AVP, [Mpa1,D-Dip2,D-Arg8]VP, [Mpa1,D-Dip2,Val4,D-Arg8]VP) are exceptionally potent antidiuretic agents with significantly prolonged activities.

2. Analogues of neurohypophyseal hormones, oxytocin and arginine vasopressin, conformationally restricted in the N-terminal part of the molecule

Wioleta Kowalczyk, et al. J Med Chem. 2006 Mar 23;49(6):2016-21. doi: 10.1021/jm058038f.

It is generally accepted that the conformation of the N-terminal part of neurohypophyseal hormones analogues is important for their pharmacological activity. In this work, we decided to investigate how the substitution of positions 2 and 3 with the ethylene-bridged dipeptide would alter the pharmacological properties of OT, [Mpa1]OT, and [Cpa1]OT (OT=oxytocin; Mpa=3-mercaptopropionic acid; Cpa=1-mercaptocyclohexaneacetic acid) and to investigate how a bulky 3,3-diphenyl-L-alanine residue incorporated in position 2 of AVP, [Mpa1]AVP, and [Cpa1]AVP (AVP=arginine vasopressin) would change the pharmacological profile of the compounds. The next analogues, [Val4]AVP, [Mpa1,Val4]AVP, and [Cpa1,Val4]AVP, had N-benzyl-L-alanine introduced at position 3. The last peptide was designed by Cys1 substitution in AVP by its sterically restricted bulky counterpart, alpha-hydroxymethylcysteine. All the peptides were tested for their in vitro uterotonic, pressor, and antidiuretic activities in the rat. The results of these assays showed that the reduction of conformational freedom of the N-terminal part of the molecule had a significant impact on pharmacological activities.

HNMR

HPLC