80182-99-6

Basic information

• Product Name: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride
• CAS NO: 80182-99-6
• Molecular Formula: C10H13NO3.ClH
• Molecular Weight: 231.679
• Mol File: 80182-99-6.mol

Chemical Properties

• CAS DataBase Reference: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(80182-99-6)
• EPA Substance Registry System: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(80182-99-6)

Safety Data

• Hazardous Substances Data: 80182-99-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 38061-23-3 α-Phenylacyl amino acid methyl ester hydrochloride 
• 69-96-5 Phenylserin 
• 100-52-7 benzaldehyde 

Downstream Products

• 17193-36-1 (2S*,3R*)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenyl-propionic acid methyl ester 
• 255896-85-6 methyl (2R,3S)-threo-N-acetyl-β-phenylserinate 
• 101469-17-4 (2S,3R)-threo-N-acetyl-β-phenylserine 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 17193-36-1 (±)-(2R,3R)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenylpropionic acid methyl ester 
• 17193-35-0 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid amide 
• 109924-94-9 Ac-(R,S)-Val-(R,S)-PhSer-OMe 
• 109924-96-1 Ac-(R,S)-Phe-(R,S)-PhSer-OMe 
• 106111-12-0 Z-Gly-PhSer-OMe 
• 100020-81-3 β-chloro-β-phenylalanine methyl ester hydrochloride 
• 80103-13-5 Boc-Gly-DL-Phe(β-OH)-OMe 
• 896735-84-5 Boc-L-Leu-DL-Phe(β-OH)-OMe 
• 227097-55-4 Boc-Aib-DL-Phe(4b-OH)-OMe 
• 930285-06-6 Boc-L-Ser(tBu)-L,D-PheSer-OMe 

Relevant articles and documents

Cyclizing pentapeptides: Mechanism and application of dehydrophenylalanine as a traceless turn-inducer

Dehydrophenylalanine is used as a traceless turn-inducer in the total synthesis of dichotomin E. Macrocyclization of the monomer is achieved in high yields and selectivity over cyclodimerization under conditions 100 times more concentrated than previously achieved. The enamide facilitates ring closing, and Rh-catalyzed hydrogenation of the unsaturated cyclic peptide results in selective formation of the natural product or its epimer, depending on our choice of phosphine ligand. NMR analysis and molecular modeling revealed that the linear peptide adopts a left-handed α-turn that preorganizes the N- and C-termini toward macrocyclization.

Dehydrodipeptide Hydrogelators Containing Naproxen N-Capped Tryptophan: Self-Assembly, Hydrogel Characterization, and Evaluation as Potential Drug Nanocarriers

In this work, we introduce dipeptides containing tryptophan N-capped with the nonsteroidal anti-inflammatory drug naproxen and C-terminal dehydroamino acids, dehydrophenylalanine (ΔPhe), dehydroaminobutyric acid (ΔAbu), and dehydroalanine (ΔAla) as efficacious protease resistant hydrogelators. Optimized conditions for gel formation are reported. Transmission electron microscopy experiments revealed that the hydrogels consist of networks of micro/nanosized fibers formed by peptide self-assembly. Fluorescence and circular dichroism spectroscopy indicate that the self-assembly process is driven by stacking interactions of the aromatic groups. The naphthalene groups of the naproxen moieties are highly organized in the fibers through chiral stacking. Rheological experiments demonstrated that the most hydrophobic peptide (containing C-terminal ΔPhe) formed more elastic gels at lower critical gelation concentrations. This gel revealed irreversible breakup, while the C-terminal ΔAbu and ΔAla gels, although less elastic, exhibited structural recovery and partial healing of the elastic properties. A potential antitumor thieno[3,2-b]pyridine derivative was incorporated (noncovalently) into the gel formed by the hydrogelator containing C-terminal ΔPhe residue. Fluorescence and F?rster resonance energy transfer measurements indicate that the drug is located in a hydrophobic environment, near/associated with the peptide fibers, establishing this type of hydrogel as a good drug-nanocarrier candidate.

Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution

The development of Ru-catalyzed asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides is described. The reaction proceeds through dynamic kinetic resolution to afford anti β-hydroxy α-amino esters with good diastereomeric ratios and high enantioselectivities.

Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts-stereoselective synthesis of anti-β-hydroxy-α-amino acids

The asymmetric hydrogenation of α-amino-β-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-β-hydroxy-α-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate.

Nitrate esters in the generation of amino acid radicals

Nitrate esters, prepared by treatment of β-hydroxy-α-amino acid derivatives with nitric acid, react with tributyltin hydride to give the corresponding alkoxyl radicals. These radicals readily undergo β-scission, providing a convenient route for the regiocontrolled production of α-carbon-centred amino acid radicals. By examining the partitioning of the alkoxyl radicals between the β-scission process and the competing hydrogen transfer reaction, it has been possible to evaluate the influence of electronic and steric effects on the β-scission reaction and the formation of the carbon-centred radicals.