37553-65-4

Basic information

• Product Name: Boc-N-methyl-L-phenylalanine
• Synonyms: BOC-L-MEPHE-OH;BOC-N-ALPHA-METHYL-L-PHENYLALANINE;BOC-MEPHE-OH;BOC-N-ME-PHENYLALANINE;BOC-N-ME-PHE-OH;BOC-N-METHYL-L-PHENYLALANINE;BOC-N-METHYL-L-PHE-OH;2-(BOC-METHYL-AMINO)-3-PHENYL-PROPIONIC ACID
• CAS NO: 37553-65-4
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Phenylalanine [Phe, F];N-Methyl Amino Acids;amino acids
• Mol File: 37553-65-4.mol

Chemical Properties

• Melting Point: 168-170 °C
• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 198.8 °C
• Appearance: /Solid
• Density: 1.146 g/cm³
• Vapor Pressure: 2.75E-07mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.90±0.10(Predicted)
• BRN: 2386503
• CAS DataBase Reference: Boc-N-methyl-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-N-methyl-L-phenylalanine(37553-65-4)
• EPA Substance Registry System: Boc-N-methyl-L-phenylalanine(37553-65-4)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 37553-65-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-N-methyl-L-phenylalanine is used as a building block for peptide synthesis, which is crucial for the development of peptide-based drugs. The growing peptide drug market necessitates fast and reliable synthesis methods, making this amino acid an essential component in the pharmaceutical sector.
Used in Research and Development:
In the field of research and development, Boc-N-methyl-L-phenylalanine serves as a valuable tool for studying the properties and functions of peptides. Its unique structure allows scientists to explore various aspects of peptide chemistry, including the design and synthesis of novel peptide-based therapeutics and the investigation of peptide-protein interactions.
Used in Chemical Synthesis:
Boc-N-methyl-L-phenylalanine is also employed in chemical synthesis, particularly in the production of complex organic molecules and compounds. Its unique structural features make it a versatile building block for creating a wide range of chemical products, from pharmaceuticals to specialty chemicals.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(19)16(4)12(13(17)18)10-11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3,(H,17,18)/t12-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 185508-99-0 (S)-N-((1R,2R)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2-methylamino-3-phenyl-propionamide 
• 37553-64-3 (S)-methyl 2-((tert-butoxycarbonyl)(methyl)amino)-3-phenylpropanoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2899-07-2 (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine 
• 1161-13-3 N-Cbz-L-Phe 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 74-88-4 methyl iodide 
• 34619-03-9 tert-butyldicarbonate 
• 618-36-0 rac-methylbenzylamine 
• 75-09-2 dichloromethane 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 66444-35-7 (S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester 
• 87876-44-6 Boc-(Me)Phe-Pip-OMe 
• 102410-61-7 Boc-MePhe-4Kps-OMe 
• 76369-91-0 Boc-MePhe-Tyr(Bzl)-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic 
• 76369-94-3 Boc-MePhe-Phe-Tyr(Bzl)-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic 
• 76369-96-5 Boc-MePhe-MePhe-Tyr(Bzl)-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic 
• 120060-98-2 Boc-D-MePhe-Thz-OTmse 
• 120060-97-1 Boc-MePhe-Thz-OTmse 
• 154561-18-9 Boc-L-MePhe-L-Pro-OPac 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 137393-05-6 N-((1,1-Dimethylethoxy)carbonyl)-N-methyl-L-phenylalanine phenylmethyl ester 
• 141611-94-1 AcAsp-Tyr-Nle-Gly-Trp-Nle-Asp-(N-Me)PheNH₂ 
• 494803-87-1 3-{2-[2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-1-hydroxy-ethyl}-indole-1-carboxylic acid tert-butyl ester 
• 494803-88-2 {1-[2-(1-benzenesulfonyl-1H-indol-3-yl)-2-hydroxy-ethylcarbamoyl]-2-phenyl-ethyl}-methyl-carbamic acid tert-butyl ester 

Relevant articles and documents

Influence of C-terminal modifications of bradykinin antagonists on their activity

In the present study we have described the synthesis and some pharmacological properties of four new analogues of bradykinin (BK). Two peptides were designed by substitution of positions 7 and 8 of known B2 antagonists with N-methyl-D-phenylala

USP30 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of USP30, and the treatment of USP30-mediated disorders.

Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity

We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.

Iridium-Catalyzed Asymmetric Hydrogenation of N-Alkyl α-Aryl Furan-Containing Imines: an Efficient Route to Unnatural N-Alkyl Arylalanines and Related Derivatives

High throughput experimentation (HTE) has enabled the rapid identification of ligand/precatalyst combinations that facilitate highly enantioselective hydrogenations of prochiral N-alkyl α-aryl ketimines containing a furyl moiety. The chiral amines obtained have proven to be modular precursors in the synthesis of unnatural mono N-alkylated arylalanines and related derivatives. (Figure presented.).

Total syntheses of cathepsin D inhibitory izenamides A, B, and C and structural confirmation of izenamide B

The first total syntheses of izenamides A, B, and C, which are depsipeptides inhibitor of cathepsin D, were accomplished. In addition, the stereochemistry of izenamide B was confirmed by our syntheses. The key features of our synthetic route involve the avoidance of critical 2,5-diketopiperazine (DKP) formation and the minimization of epimerization during the coupling of amino acids for the target peptides.

Gram-Scale Solution-Phase Synthesis of Heptapeptide Side Chain of Teixobactin 1

We report herein a scalable synthesis of linear heptapeptide side chain of the depsipeptide natural product teixobactin through solution phase. The synthesis of heptapeptide was achieved through an efficient coupling of suitably protected tripeptide and tetrapeptide comprising of three d-amino acids and four usual l-amino acid subunits.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

D-amino acid position influences the anticancer activity of galaxamide analogs: An apoptotic mechanism study

Galaxamide, an extract from Galaxaura filamentosa, is a cyclic pentapeptide containing five L-leucines. Due to the particular cyclic structure and the excellent anticancer activity, synthesis of Galaxamide and its analogs and their subsequent bio-applications have attracted great attention. In the present work, we synthesized six Galaxamide analogs by replacing one of the L-leucines with phenylalanine and varying the D-amino acid position. The anticancer effect of the synthesized Galaxamide analogs was tested against four in vitro human cancer cell lines, human hepatocellular cells (HepG2), human breast cancer cell (MCF-7), human breast adenocarcinoma cells (MDA-MB-435) and a human cervical carcinoma cell line (Hela). Results showed that Galaxamide analogs with differentD-amino acid positions displayed distinct anticancer potential. The Galaxamide analog containing D-amino acid at position 5 (Analog-6) presented the strongest anticancer activity. The mechanism study revealed that Analog-6 could cause the early apoptosis of HepG2 cells by inhibiting their growth in the sub-G1 stage of the cell cycle and induce the chromatin condensation and fragmentation, which can be seen as 68% of HepG2 cells inhibited in the sub-G1 stage. Moreover, a mitochondria-mediated pathway was found to be involved in the apoptotic process of Analog-6 on HepG2 cells.

Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates

Abstract: A new series of side chain-modified 4-aminoquinolines were synthesized and screened for in vitro antiplasmodial activity against both chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Among the series, compounds 30 and 31 showed significant inhibition of parasite growth against K1 strain of P. falciparum with IC50 values 0.28 and 0.31?μM, respectively, whereas compounds 34, 35, and 38 exhibited superior activity against K1 strain with IC50 values 0.18, 0.22, and 0.17?μM, respectively, as compared to 0.255?μM for chloroquine (CQ). All the compounds displayed good resistance factor between 1.54 and >34.48 as against 51.0 for CQ. All these analogues were found to form strong complex with hematin and inhibited the β-hematin formation in vitro, suggesting that this class of compounds act on a heme polymerization target. Overall results suggest that present series of compounds appear to be promising for further lead optimization to obtain compounds active against drug-resistant parasites. Graphical Abstract: [Figure not available: see fulltext.]

Design, synthesis, and optimization of balanced dual NK1/NK 3 receptor antagonists

In connection with a program directed at potent and balanced dual NK 1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pKi values of 8.6 and 8.1, respectively.