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
• Article Data: 33

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

Chemical Properties

Off-white solid

Uses

N-BOC-N-Methyl-L-phenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

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

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 74-88-4 methyl iodide 
• 75-09-2 dichloromethane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 77-78-1 dimethyl sulfate 
• 185508-99-0 (S)-N-((1R,2R)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2-methylamino-3-phenyl-propionamide 
• 618-36-0 rac-methylbenzylamine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 211191-12-7 [2-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-oxo-ethyl]-methyl-carbamic acid tert-butyl ester 
• 13734-36-6 N-(tert-butoxycarbonyl)sarcosine 
• 149206-46-2 (4S)-4-Benzyl-N-tert-butyloxycarbonyl-1,3-oxazolidin-5-one 
• 673-06-3 D-(R)-phenylalanine 

Downstream Products

• 94779-56-3 Boc-MePhe-Gly-OBzl 
• 137393-05-6 N-((1,1-Dimethylethoxy)carbonyl)-N-methyl-L-phenylalanine phenylmethyl ester 
• 169545-90-8 (S)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 213335-56-9 ((R)-1-Ethylcarbamoyl-2-phenyl-ethyl)-methyl-carbamic acid tert-butyl 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 
• 639457-75-3 2-[2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester 
• 264128-49-6 (S)-tert-butyl (1-hydroxy-3-phenylpropan-2-yl)(methyl)carbamate 
• 1027178-53-5 2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionic acid 1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester 
• 723296-11-5 2-(tert-butoxycarbonyl-methyl-amino)-3-phenyl-propionic acid 1-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-pent-4-enyl ester 
• 61125-52-8 (+/-)-cis-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione 

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

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.

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.