66617-58-1

Basic information

• Product Name: BOC-PHE-OBZL
• Synonyms: N-ALPHA-T-BUTOXYCARBONYL-L-PHENYLALANINE BENZYL ESTER;BOC-PHE-OBZ;BOC-PHE-OBZL;BOC-PHENYLALANINE-OBZL;BOC-L-PHENYLALANINE BENZYL ESTER;N-tert-butoxycarbonylphenylalanine benzyl ester;N-tert-Butoxycarbonyl-L-phenylalanine benzyl ester
• CAS NO: 66617-58-1
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.43
• Mol File: 66617-58-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 65℃
• Boiling Point: 500.2°Cat760mmHg
• Flash Point: 256.3°C
• Appearance: /
• Density: 1.129g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: Store at RT.
• CAS DataBase Reference: BOC-PHE-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-PHE-OBZL(66617-58-1)
• EPA Substance Registry System: BOC-PHE-OBZL(66617-58-1)

Safety Data

• Hazardous Substances Data: 66617-58-1(Hazardous Substances Data)

Usage

General Description

BOC-Phe-OBzl is a chemical compound consisting of a benzyl-protected phenylalanine derivative. It is commonly used in peptide synthesis as a protecting group for the amino acid phenylalanine. The BOC (tert-butyloxycarbonyl) group serves to protect the amine group of phenylalanine, while the OBzl (benzyl ester) group protects the carboxylic acid group. BOC-PHE-OBZL allows for efficient peptide synthesis by protecting specific chemical groups and facilitating the coupling of amino acids in a controlled manner. BOC-Phe-OBzl is a key reagent in the development of peptides and peptidomimetics for various biological and pharmaceutical applications.

InChI:InChI=1/C21H25NO4/c1-21(2,3)26-20(24)22-18(14-16-10-6-4-7-11-16)19(23)25-15-17-12-8-5-9-13-17/h4-13,18H,14-15H2,1-3H3,(H,22,24)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 100-39-0 benzyl bromide 
• 1155946-51-2 C₂₂H₂₂N₃O₂P 
• 108-88-3 toluene 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-44-7 benzyl chloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 100-51-6 benzyl alcohol 
• 94882-74-3 benzyl 2(S)-(tert-butoxycarbonylamino)-3-p-toluenesulfonylpropionate 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 
• 3695-68-9 L-serine benzyl ester benzenesulfonate salt 
• 34101-07-0 (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one 
• 31139-36-3 dibenzyl dicarbonate 

Downstream Products

• 962-39-0 L-Phenylalanine benzyl ester 
• 16879-80-4 tert-butyl ((S)-1-oxo-1-(((S)-3-oxo-1,4-diphenylbutan-2-yl)amino)-3-phenylpropan-2-yl)carbamate 
• 141774-74-5 2-phenyl-1-pyridin-2-ylmethylcarbamoyl ethyl carbamic acid tert butyl ester 
• 131941-62-3 Val-Phe-OBzl 
• 70669-15-7 benzyl (tert-butoxycarbonyl)-L-valyl-L-phenylalaninate 
• 70691-56-4 L-leucyl-L-phenylalanine methyl ester hydrochloride 
• 218785-75-2 Fmoc-L-Ala-L-Phe-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Relevant articles and documents

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

A novel route towards cycle-tail peptides using oxime resin: Teaching an old dog a new trick

Two anabaenopeptins, Schizopeptin 791 and anabaenopeptin NZ825, have similar structural features and have been synthesized via a novel acid-catalyzed head-to-side-chain concomitant cyclization/cleavage reaction on oxime resin. The methodology gave rapid access to the anabaenopeptin scaffold by taking advantage of a combined solid-phase/solution-phase synthetic strategy. Also, as side-products of the synthesis, large C2-symmetric 38-member cyclic peptides ring bearing two endocyclic lysine side-chains were isolated, constituting a novel cyclic peptide scaffold.

Self-Assembly of Tetraphenylalanine Peptides

Three different tetraphenylalanine (FFFF) based peptides that differ at the N- and C-termini have been synthesized by using standard procedures to study their ability to form different nanoassemblies under a variety of conditions. The FFFF peptide assembles into nanotubes that show more structural imperfections at the surface than those formed by the diphenylalanine (FF) peptide under the same conditions. Periodic DFT calculations (M06L functional) were used to propose a model that consists of three FFFF molecules defining a ring through head-to-tail NH3+?-OOC interactions, which in turn stack to produce deformed channels with internal diameters between 12 and 16 ?. Depending on the experimental conditions used for the peptide incubation, N-fluorenylmethoxycarbonyl (Fmoc) protected FFFF self-assembles into a variety of polymorphs: ultra-thin nanoplates, fibrils, and star-like submicrometric aggregates. DFT calculations indicate that Fmoc-FFFF prefers a parallel rather than an antiparallel β-sheet assembly. Finally, coexisting multiple assemblies (up to three) were observed for Fmoc-FFFF-OBzl (OBzl = benzyl ester), which incorporates aromatic protecting groups at the two peptide terminals. This unusual and noticeable feature is attributed to the fact that the assemblies obtained by combining the Fmoc and OBzl groups contained in the peptide are isoenergetic. Variety show! Three different tetraphenylalanine-based peptides that differ at the N- and C-termini have been synthesized by using standard procedures to study their ability to form different nanoassemblies (e.g., nanotubes, see figure) under a variety of conditions.