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D-Phenylalanine methyl ester hydrochloride is an organic compound that serves as an essential building block in the synthesis of various pharmaceuticals and chemical compounds. It is a white solid with unique chemical properties that make it suitable for a range of applications in different industries.

13033-84-6

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13033-84-6 Usage

Uses

Used in Pharmaceutical Industry:
D-Phenylalanine methyl ester hydrochloride is used as a key intermediate in the synthesis of pharmaceuticals for various therapeutic applications. Its ability to form amidines through copper-catalyzed three-component coupling with sulfonyl azides and alkynes makes it a valuable compound in the development of new drugs.
Used in Organic Synthesis:
In the field of organic chemistry, D-Phenylalanine methyl ester hydrochloride is used as a versatile reagent for the preparation of a wide range of chemical compounds. Its unique chemical properties allow it to be employed in various synthetic pathways, contributing to the development of novel molecules with potential applications in various industries.
Used in Research and Development:
D-Phenylalanine methyl ester hydrochloride is also utilized in research and development laboratories for the exploration of new chemical reactions and the synthesis of innovative compounds. Its role in the preparation of amidines and other complex molecules makes it an essential tool for scientists working on the cutting edge of chemical research.

Check Digit Verification of cas no

The CAS Registry Mumber 13033-84-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,0,3 and 3 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13033-84:
(7*1)+(6*3)+(5*0)+(4*3)+(3*3)+(2*8)+(1*4)=66
66 % 10 = 6
So 13033-84-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h2-6,9H,7,11H2,1H3;1H/t9-;/m1./s1

13033-84-6 Well-known Company Product Price

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  • TCI America

  • (P1725)  D-Phenylalanine Methyl Ester Hydrochloride  >98.0%(HPLC)(T)

  • 13033-84-6

  • 5g

  • 390.00CNY

  • Detail
  • TCI America

  • (P1725)  D-Phenylalanine Methyl Ester Hydrochloride  >98.0%(HPLC)(T)

  • 13033-84-6

  • 25g

  • 1,200.00CNY

  • Detail
  • Alfa Aesar

  • (H25920)  D-Phenylalanine methyl ester hydrochloride, 99%   

  • 13033-84-6

  • 5g

  • 417.0CNY

  • Detail
  • Alfa Aesar

  • (H25920)  D-Phenylalanine methyl ester hydrochloride, 99%   

  • 13033-84-6

  • 25g

  • 1264.0CNY

  • Detail
  • Aldrich

  • (525472)  D-Phenylalaninemethylesterhydrochloride  98%

  • 13033-84-6

  • 525472-5G

  • 590.85CNY

  • Detail
  • Aldrich

  • (525472)  D-Phenylalaninemethylesterhydrochloride  98%

  • 13033-84-6

  • 525472-10G

  • 1,084.59CNY

  • Detail

13033-84-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name D-Phenylalanine methyl ester hydrochloride

1.2 Other means of identification

Product number -
Other names H-D-Phe-OMe·HCl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13033-84-6 SDS

13033-84-6Relevant articles and documents

Synthesis and antiviral activity of novel glycyrrhizic acid conjugates with D-amino acid esters

Fayrushina,Baltina,Baltina,Konovalova,Petrova,Eropkin, M. Yu.

, p. 456 - 462 (2017)

Glycyrrhizic acid (GA) conjugates with methyl and ethyl esters of D-amino acids (D-Trp, D-Phe, D-Tyr, D-Val, D-Leu) have been synthesized by the activated esters method using mixtures of N-hydroxybenzotriazole or N-hydroxysuccinimide with N,N′-dicyclohexylcarbodiimide. GA conjugate with D-Trp ethyl ester exhibited antiviral activity against influenza viruses A/H3N2, A/H1N1/pdm09, A/H5N1, B (SI > 10–29), and HRSV (SI > 25). GA conjugate with D-Trp methyl ester inhibited influenza virus A/H1N1/pdm09 (SI > 30).

RETRACTED ARTICLE: Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrug of 5-aminosalicylic acid with d-phenylalanine for colon specific drug delivery in inflammatory bowel disease

Dhaneshwar, Suneela S.,Gairola, Neha,Kandpal, Mini,Bhatt, Lokesh,Vadnerkar, Gaurav,Kadam

, p. 1897 - 1902 (2007)

Mutual azo prodrug of 5-aminosalicylic acid with d-phenylalanine was synthesized by coupling d-phenylalanine with salicylic acid, for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. The structure of synthesized prodrug was

Optical Resolution of Amino Acid Esters by N-Protected Aspartylphenylalanine Esters

Oyama, Kiyotaka,Itoh, Mikio,Nonaka, Yuji

, p. 1751 - 1754 (1992)

A new method was studied for optical resolution of racemic amino acids esters by using, as resolving agents, N-protected L-α-aspartyl-L-phenylalanine alkyl esters, typically, N-benzyloxycarbonyl-L-α-aspartyl-L-phenylalanine methyl ester, the precursor to the synthetic sweetener aspartame.Thus, when the dipeptide and racemic amino acid ester were mixed in solvents, precipitation took place by formation of salt preferentially with D-amino acid ester to effect the optical resolution.

Catalysts and temperature driven melt polycondensation reaction for helical poly(ester-urethane)s based on natural L-amino acids

Anantharaj, Santhanaraj,Jayakannan, Manickam

, p. 1065 - 1077 (2016)

Catalyst and temperature driven melt polycondensation reaction was developed for natural L-amino acid monomers to produce new classes of poly(ester-urethane)s. Wide ranges of catalysts from alkali, alkali earth metal, transition metal and lanthanides were developed for the condensation of amino acid monomers with diols to yield poly(ester-urethane)s. A-B Diblock and A-B-A triblock species were obtained by carefully choosing mono- or diols in model reactions. More than two dozens of transition metal and lanthanide catalysts were identified for the polycondensation to yield high molecular weight poly(ester-urethane)s. Theoretical studies revealed that the carbonyl carbon in ester possessed low electron density compared to the carbonyl carbon in urethane which driven the thermo-selective polymerization process. Optical purity of the L-amino acid residues in the melt polycondensation process was investigated using D- and L-isomers and the resultant products were analyzed by chiral-HPLC and CD spectroscopy. CD analysis revealed that the amino acid based polymers were self-assembled as β-sheet and polyproline type II secondary structures. Electron and atomic force microscopic analysis confirmed the formation of helical nano-fibrous morphology in poly(ester-urethane)s. The newly developed melt polycondensation process is very efficient and optimized for wide range of catalysts to produce diverse polymer structures from natural L-amino acids.

Modular Fragment Synthesis and Bioinformatic Analysis Propose a Revised Vancoresmycin Stereoconfiguration

Adamek, Martina,Essig, Sebastian,Kurz, Michael,Menche, Dirk,Sch?nenbroicher, Max,Seul, Maximilian,Spindler, Stefanie,Wingen, Lukas M.,Ziemert, Nadine

supporting information, p. 1175 - 1180 (2021/01/13)

Elaborate fragments of the proposed stereostructure of the complex polyketide antibiotic vancoresmycin have been synthesized in a stereoselective fashion based on a modular and convergent approach. Significant nuclear magnetic resonance differences in one of these subunits compared with the natural product question the proposed stereoconfiguration. Consequently, an extensive bioinformatics analysis of the biosynthetic gene cluster was carried out, leading to a revised stereoconfigurational proposal for this highly potent antibiotic.

Convenient method for the synthesis of some novel chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties

Matam, Sivakumar,Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal,Lohanathan, Bharathi Priya,Viswanadhan, Vijaya Padma,Makala, Himesh,Venkatasubramanian, Ulaganathan

supporting information, p. 569 - 579 (2020/12/11)

Ten chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives 6a-6j have been synthesized from optically pure amino methyl phenol 5 and 4-nitrophenyl chloroformate. These derivatives 6a-6j are characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral techniques. Optical purity of these derivatives was confirmed by chiral HPLC method. Ten synthesized ester derivatives 6a-6j were screened for their in vitro antioxidant activity. Among the compounds 6b-d and 6h-j have exhibited comparable antioxidant activity with ascorbic acid as a standard. Compounds 6a and 6e-g have shown moderate antioxidant activity. Further, the in vitro cytotoxicity of these compounds were studied through MTT cell proliferation assay in addition the effect on LDH leakage and NO release. Among the derivatives, 6j showed extremely best activity and the IC50 value (12.54 ± 0.71 μM) is very close to doxorubicin (7.2 ± 0.58 μM) as a standard. Compounds 6b, 6h, and 6i showed better inhibition next to compound 6j on the viability of HepG2 cells with an IC50 value (μM) of 56.02 ± 1.4, 41.76 ± 0.58, and 38.17 ± 0.34, respectively. Also, molecular docking studies have been carried out with STAT-3 (PDB ID: 1BG1) and BCL-2 (PDB ID: 4AQ3) proteins against the four active compounds 6b, 6h, 6i, and 6j. The binding energies of the tested compounds were in the range of ?7.76 to ?8.41 kcal/mol, which is very close to doxorubicin (?8.53 kcal/mol) as a standard. These molecular docking results are in good agreement with the in vitro studies.

Mechanoresponsive, proteolytically stable and biocompatible supergelators from ultra short enantiomeric peptides with sustained drug release propensity

Basu, Anindya,Christman, Ryann M.,Duttkonar, Anita,Harjit, Jeena,Mehra, Radha Rani,Mishra, Anil K.,Tiwari, Amit K.

, p. 6346 - 6354 (2020/05/13)

Stimuli-responsive low molecular weight hydrogelators attract immense interest from diverse segments of biomedicine and biotechnology. Distinctly, herein we report newly synthesized enantiomeric ultrashort peptides of general formula Me-(CH2)8-CO-NH-CH(X)-COOH, where X = CH2Ph in hydrogelators I (l-Phe) and II (d-Phe) respectively, which display excellent self-assembling propensity in physiological buffer at room temperature. Interestingly these biomolecules were endowed with mechanoresponsiveness, injectability and high mechanical integrity as confirmed by rheological measurements. Importantly they revealed resistance towards proteolytic degradation. Indeed dose dependent cell viability studies using MTT assay in four different cell lines, namely PANC-1, S1, HCT-116 and MDAMB-231, further confirmed the biocompatibility of the hydrogelators in vitro. The structural aspect of β-sheets of the hydrogelators was concluded on the basis of temperature dependent NMR, IR, PXRD and computational studies. We developed a user friendly delivery system, hydrogel nanoparticles (HNPs), with our mechanoresponsive and biocompatible hydrogelators, as these particles exhibited promising influence due to their enhanced surface area. Also the HNPs revealed excellent drug release kinetics for the model drugs 5FU/doxorubicin under physiological conditions in a sustained manner depending on the physicochemical parameters of the drugs. Taking these results together we envision that our designed hydrogelators and the delivery vehicle generated therefrom might represent a promising tool for administration of significant drug concentrations at lesion sites for a prolonged period, thus providing a better strategy for quick pain relief, rapid recovery and reduced systemic side effects.

In search of bioinspired hydrogels from amphiphilic peptides: A template for nanoparticle stabilization for the sustained release of anticancer drugs

Mehra, Radha Rani,Tiwari, Priyanka,Basu, Anindya,Duttkonar, Anita

, p. 11666 - 11678 (2019/07/31)

The development of potent stimuli-responsive hydrogels has rapidly expanded in the last decades due to their diversified applications in the field of biomedicines. In accordance with this drift, herein, we aimed at modulating a series of amphiphilic peptide analogues with the general formula Me-(CH2)14-CO-NH-CH(X)-COOH, where X = CH2Ph in hydrogelators I (l-Phe) and II (d-Phe) and X = CH2Ph(OH) in hydrogelator III (l-Tyr), which displayed an excellent propensity to immobilize water at room temperature with a minimum gelation concentration of 0.04%/0.05%/0.02% w/v for hydrogelators I-III, respectively, regardless of their configuration at the C-terminal centre. To validate this threshold concentration difference, we performed computational analysis that demonstrated the ability of the side-chains of hydrogelators I and III to remain highly planar with the methylene units of the amphiphile and aromatic rings, promoting favourable correspondence through van der Waals forces and pi-pi stacking. Consequently hydrogelators I and III self-assembled in an ordered organisation superior to hydrogelator II. Furthermore, the spectroscopic and microscopic experiments revealed that the hydrogelators manifested a β-sheet conformation and nanofibrous morphology at the supramolecular level. As observed visually and additionally confirmed by differential scanning calorimetry (DSC) and rheological measurements, the hydrogels exhibited thermo-reversibility, injectability and high mechanical strength. Importantly, these biomaterials were also found to be resistant towards proteolytic degradation and non-cytotoxic in the cell line HEK 293 using a dose-dependant cell viability assay. To date, the development of a structured approach for the release of drugs in a predictable manner from an optimised formulation, using peptide-based hydrogel nanoparticles as a delivery system remains in its infancy. Hence, we developed hydrogel nanoparticles (HNPs) with our fabricated amphiphilic peptides that exploited the weak noncovalent interactions for their fabrication, unlike other cross-linked polymers that require strong covalent or ionic bonds for their formation. Interestingly, the as-synthesized nanoparticles showed an unprecedented ability to release the anticancer drugs 5-fluoro uracil/doxorubicin at physiological conditions depending on the physico-chemical parameters of the drugs. We believe that the reported injectable, biocompatible, amphiphilic peptide-based hydrogels hold future promise as a potential tool to transport drugs to a targeted site at a greater concentration, thus relieving the patient from surgical injury and simultaneously aiding in a faster recovery.

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

Yen, Andy,Pham, Anh Hoang,Larin, Egor M.,Lautens, Mark

supporting information, p. 7549 - 7553 (2019/10/02)

The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.

((S)-3-Mercapto-2-methylpropanamido)acetic acid derivatives as metallo-β-lactamase inhibitors: Synthesis, kinetic and crystallographic studies

Liu, Sha,Jing, Li,Yu, Zhu-Jun,Wu, Chengyong,Zheng, Yongxiang,Zhang, En,Chen, Qiang,Yu, Yamei,Guo, Li,Wu, Yong,Li, Guo-Bo

, p. 649 - 660 (2018/02/10)

The emergence and global spread of metallo-β-lactamase (MBL) mediated resistance to almost all β-lactam antibacterials poses a serious threat to public health. Since no clinically useful MBL inhibitors have been reported, there is an urgent need to develop new potent broad-spectrum MBL inhibitors effective against antibacterial resistance. Herein, we synthesized a set of 2-substituted ((S)-3-mercapto-2-methylpropanamido) acetic acid derivatives, some of which displayed potent inhibition with high ligand efficiency to the clinically relevant MBL subtypes, Verona Integron-encoded MBL (VIM)-2 and New Delhi MBL (NDM)-1. Kinetic studies revealed that the inhibitors are not strong zinc chelators in solution, and they bind reversibly to VIM-2 but dissociate very slowly. Crystallographic analyses revealed that they inhibit VIM-2 via chelating the active site zinc ions and interacting with catalytically important residues. Further cell- and zebrafish-based assays revealed that the inhibitors slightly increase susceptibility of E. coli cells expressing VIM-2 to meropenem, and they have no apparent toxicity to the viability of HEK293T cells and the zebrafish embryogenesis.

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