100564-78-1

Basic information

• Product Name: Boc-L-homophenylalanine
• Synonyms: 2-tert-Butoxycarbonylamino-4-(S)-phenylbutyric acid;BOC-L-HOMOPHE;BOC-L-HOMOPHENYL-ALA;Boc-Hphe-OH ,98%;Boc-HoPhe-PH;Benzenebutanoic acid, a-[[(1,1-diMethylethoxy)carbonyl]aMino]-,(;(S)-2-(N-(tert-butoxycarbonyl)aMino)-4-phenylbutanoic acid;Boc-Hphe
• CAS NO: 100564-78-1
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Amino Acids
• Mol File: 100564-78-1.mol

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 439.6 °C at 760 mmHg
• Flash Point: 219.7 °C
• Appearance: /
• Density: 1.139
• Vapor Pressure: 1.67E-08mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol.
• PKA: 3.95±0.10(Predicted)
• BRN: 3653506
• CAS DataBase Reference: Boc-L-homophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-homophenylalanine(100564-78-1)
• EPA Substance Registry System: Boc-L-homophenylalanine(100564-78-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 100564-78-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Boc-L-homophenylalanine is used as a reagent in organic synthesis for its ability to participate in a wide range of chemical reactions. The presence of the Boc group allows for selective protection and deprotection steps, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Boc-L-homophenylalanine is used as a building block for the development of novel drugs. Its unique structure and reactivity contribute to the design and synthesis of new pharmaceutical compounds with potential therapeutic applications.
Used in the Preparation of Proteasome Inhibitors:
Specifically, Boc-L-homophenylalanine is utilized in the synthesis of piperidine-containing peptidyl proteasome inhibitors. These inhibitors are of significant interest due to their potential as therapeutic agents in the treatment of various diseases, including cancer and neurodegenerative disorders. The incorporation of Boc-L-homophenylalanine into these inhibitors allows for the exploration of structure-activity relationships and the optimization of their pharmacological properties.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(19)16-12(13(17)18)10-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m0/s1

Upstream product

• 133832-78-7 3-(tert-Butoxycarbonylamino)-1,2,3-tridesoxy-1-phenyl-D-manno-heptitol 
• 116611-56-4 tert-butyl (R)-(1-hydroxy-4-phenylbutan-2-yl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 91-00-9 Benzhydrylamine 
• 240420-40-0 tert-butyl (4R)-2,2-dimethyl-4-(2-phenylethyl)-1,3-oxazolidine-3-carboxylate 
• 872728-70-6 (1R,4'S)-N-tert-butoxycarbonyl-1-(2',2'-dimethyl-[1',3']-dioxolan-4'-yl)-3-phenylpropylamine 
• 115378-31-9 tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate 
• 591-50-4 iodobenzene 
• 132652-65-4 tert-butyl 2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-oxazolane-3-carboxylate 
• 133625-99-7 (2R,3E)-2-(tert-butyloxycarbonylamino)-4-phenyl-3-buten-1-ol 
• 116611-49-5 ((S)-1-Hydroxymethyl-2-phenylsulfanyl-ethyl)-carbamic acid tert-butyl ester 
• 116696-85-6 (2S)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 116611-63-3 methyl N-(tert-butoxycarbonyl)-O-(tetrahydro-2H-pyran-2-yl)-L-serinate 

Downstream Products

• 162126-44-5 (3-phenyl-1-{[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-carbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 254882-54-7 N-tert-butoxycarbonyl-D-homophenylalanine 3-quinolylamide 
• 240420-27-3 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-4-phenylbutanoate 
• 116611-56-4 tert-butyl (R)-(1-hydroxy-4-phenylbutan-2-yl)carbamate 

Relevant articles and documents

Quantum Chemical-Based Protocol for the Rational Design of Covalent Inhibitors

We propose a structure-based protocol for the development of customized covalent inhibitors. Starting from a known inhibitor, in the first and second steps appropriate substituents of the warhead are selected on the basis of quantum mechanical (QM) computations and hybrid approaches combining QM with molecular mechanics (QM/MM). In the third step the recognition unit is optimized using docking approaches for the noncovalent complex. These predictions are finally verified by QM/MM or molecular dynamic simulations. The applicability of our approach is successfully demonstrated by the design of reversible covalent vinylsulfone-based inhibitors for rhodesain. The examples show that our approach is sufficiently accurate to identify compounds with the desired properties but also to exclude nonpromising ones.

A short enantioselective synthesis of N-Boc-α-amino acids from epoxy alcohols

A new and efficient enantioselective synthesis of Boc-α-amino acids has been developed. Starting from an enantiomerically enriched epoxy alcohol the sequence involves a regioselective nucleophilic epoxide opening by diphenylmethylamine (benzhydrilamine), hydrogenolysis/ protection of the amino group, and oxidation of the diol moiety.

Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A New Regio- And Stereoselective Strategy to δ-Functionalized β-Amino Alcohols

An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and in Vivo Studies

Rhodesain is a major cysteine protease of Trypanosoma brucei rhodesiense, a pathogen causing Human African Trypanosomiasis, and a validated drug target. Recently, we reported the development of α-halovinylsulfones as a new class of covalent reversible cysteine protease inhibitors. Here, α-fluorovinylsulfones/-sulfonates were optimized for rhodesain based on molecular modeling approaches. 2d, the most potent and selective inhibitor in the series, shows a single-digit nanomolar affinity and high selectivity toward mammalian cathepsins B and L. Enzymatic dilution assays and MS experiments indicate that 2d is a slow-tight binder (Ki = 3 nM). Furthermore, the nonfluorinated 2d-(H) shows favorable metabolism and biodistribution by accumulation in mice brain tissue after intraperitoneal and oral administration. The highest antitrypanosomal activity was observed for inhibitors with an N-terminal 2,3-dihydrobenzo[b][1,4]dioxine group and a 4-Me-Phe residue in P2 (2e/4e) with nanomolar EC50 values (0.14/0.80 μM). The different mechanisms of reversible and irreversible inhibitors were explained using QM/MM calculations and MD simulations.

N-ALKOXYAMIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

N-alkoxyamide conjugates as imaging agents

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation

Novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation were developed; some of them possess Ki values in the micromolar range. We studied the structure-activity relationship of these derivatives and we performed docking studies, which allowed us to find out the key interactions established by the inhibitors with the target enzyme. Biological results indicate that the nature of the P2 and P3 substituents and their binding to the S2/S3 pockets is strictly interdependent.

Synthesis of γ-oxo γ-aryl and γ-aryl α-amino acids from aromatic aldehydes and serine

γ-Oxo α-amino acids and γ-aryl α-amino acids are compounds with very interesting biological properties and are active components of many drug molecules. Oxo amino acids are also used as synthetic precursors for a number of unnatural amino acids and amino alcohols. We report a very efficient synthesis of such compounds through the coupling of aromatic dithianes, prepared from aromatic aldehydes and an iodide derivative of serine. The dithiane groups in compounds thus obtained can be either hydrolyzed or reduced to generate 4-oxo-4-aryl or 4-aryl 2-amino butanol derivatives, respectively, which, on further transformations, can be converted into the title compounds. Starting with L-serine provides the corresponding D-amino acids with complete enantiopurity. The reported method is economically viable and complements the existing methods, which rely largely on cross-coupling reactions.

N-ALKOXYAMIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

HYDRAZIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to diagnostic agents. More specifically, the disclosure is directed to compounds, diagnostic agents, compositions, and kits for detecting and/or imaging and/or monitoring a pathological disorder associated with coronary plaque, carotid plaque, aortic plaque, plaque of the arterial vessel, aneurism, vasculitis, and other diseases of the arterial wall. In addition, the disclosure is directed to methods of detecting and/or imaging and/or monitoring changes in the arterial wall, including expansive and constrictive remodeling, total vessel wall area, internal lumen size, and exterior artery perimeter.