114873-06-2

Basic information

• Product Name: BOC-L-3-Methylphe
• Synonyms: Boc-L-3-Me-Phe-OH;BOC-L-3-METHYL-PHE-OH;L-Phenylalanine,N-[(1,1-diMethylethoxy)carbonyl]-3-Methyl-;Boc-L-3-Me-Phe-OH Boc-3-Methy-L-Phenylalanine;Boc-3-Methyl-L-phenylalanine Boc-M-Me-Phe-OH;N-Boc-3-Methyl-L-phenylalanine, 98%;BOC-PHE(3-ME)-OH, >=98.0%;(S)-2-Boc-2-amino-3-(3-methylphenyl)propionic acid
• CAS NO: 114873-06-2
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Phenylalanine analogs and other aromatic alpha amino acids;a-amino;Amino Acids
• Mol File: 114873-06-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 70°C
• Boiling Point: 439.9 °C at 760 mmHg
• Flash Point: 219.9 °C
• Appearance: /Solid
• Density: 1.14 g/cm³
• Vapor Pressure: 1.62E-08mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.92±0.10(Predicted)
• BRN: 8989098
• CAS DataBase Reference: BOC-L-3-Methylphe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-3-Methylphe(114873-06-2)
• EPA Substance Registry System: BOC-L-3-Methylphe(114873-06-2)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 114873-06-2(Hazardous Substances Data)

Usage

General Description

BOC-L-3-Methylphe, also known as Boc-3-Methyl-L-phenylalanine, is a chemical compound used in organic synthesis and peptide chemistry. It is a derivative of phenylalanine, an essential amino acid, with a tert-butyloxycarbonyl (BOC) protective group attached to the amino group. BOC-L-3-Methylphe is commonly used as a building block for the synthesis of peptide and protein molecules. It is also used in the pharmaceutical industry for the production of pharmaceutical intermediates and active pharmaceutical ingredients. Additionally, this compound has applications in the field of medicinal chemistry, as it can be used to modify the properties of bioactive molecules.

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

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2283-42-3 (S)-2-amino-3-(3-methylphenyl)propionic acid 
• 102831-44-7 diethyl tert-butoxycarbonylaminomalonate 
• 620-13-3 1-bromomethyl-3-methyl-benzene 

Downstream Products

• 719274-94-9 2-amino-N-(2-benzyloxy-1-cyano-ethyl)-3-m-tolyl-propionamide 
• 1026055-75-3 5-[(R)-2-((S)-2-Amino-3-m-tolyl-propionylamino)-2-cyano-ethoxymethyl]-furan-2-carboxylic acid allyl ester 
• 719274-97-2 4-[(R)-2-((S)-2-Amino-3-m-tolyl-propionylamino)-2-cyano-ethoxymethyl]-benzoic acid allyl ester 
• 225122-61-2 N-[2-[(3-(allyloxycarbonyl)phenyl)methoxy]-1(S)-cyanoethyl]-3-methyl-L-phenylalaninamide 
• 389600-29-7 N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide 
• 1026341-39-8 3-[(R)-2-((S)-2-Benzoylamino-3-m-tolyl-propionylamino)-2-cyano-ethoxymethyl]-benzoic acid allyl ester 

Relevant articles and documents

SULPHONYLAMINO DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE

A compound of formula (I), wherein R1 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, heteropolycyclyl or polycyclyl, any of which is optionally substituted with alkyl, heteroaryl, aryl or -O-aryl; R2 is alkyl, alkenyl or aryl, any of which is optionally substituted with hydroxy, halogen, aryl, heteroaryl, cycloalkyl, cycloalkenyl, -C(O)NH-aryl, heterocycloalkyl, heterocycloalkenyl, heteropolycyclyl or polycyclyl; R3 is hydrogen or aryl; R4 is alkyl, alkenyl, alkoxy, alkylthio or aryl, any of which is optionally substituted with hydroxy, aryl, heteroaryl, cycloalkyl, cycloalkenyl, thioalkyl, heterocycloalkyl, heterocycloalkenyl, heteropolycyclyl or polycyclyl; R5 is hydrogen or an alkyl or alkenyl group optionally substituted with hydroxy, aryl, -C(O)O- alkyl or -C(O)NH- alkyl; or R4-C-R5 taken together form cycloalkyl, cycloalkenyl or polycyclyl, any of which is optionally substituted with alkyl or hydroxyalkyl; R6 is hydrogen, alkyl, -alkyl-aryl or -alkyl-heteroaryl; or a pharmaceutically-acceptable salt thereof.

Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design

Cathepsin B is a member of the papain superfamily of cysteine proteases and has been implicated in the pathology of numerous diseases, including arthritis and cancer. As part of an effort to identify potent, reversible inhibitors of this protease, we examined a series of dipeptidyl nitriles, starting with the previously reported Cbz-Phe-NH-CH2CN (19, IC50 = 62 μM). High-resolution X-ray crystallographic data and molecular modeling were used to optimize the P1, P2, and P3 substituents of this template. Cathepsin B is unique in its class in that it contains a carboxylate recognition site in the S2′ pocket of the active site. Inhibitor potency and selectivity were enhanced by tethering a carboxylate functionality from the carbon α to the nitrile to interact with this region of the enzyme. This resulted in the identification of compound 10, a 7 nM inhibitor of cathepsin B, with excellent selectivity over other cysteine cathepsins.