100442-89-5

Basic information

• Product Name: BOC-3-(1-PYRENYL)-L-ALANINE
• Synonyms: N-ALPHA-T-BUTOXYCARBONYL-3-(1-PYRENYL)-L-ALANINE;BOC-ALA(1-PYN)-OH;BOC-ALA(1-PYRENYL)-OH;BOC-3-(1-PYRENYL)-L-ALANINE
• CAS NO: 100442-89-5
• Molecular Formula: C₂₄H₂₃NO₄
• Molecular Weight: 389.44
• Mol File: 100442-89-5.mol

Chemical Properties

• Boiling Point: 614.8±48.0 °C(Predicted)
• Appearance: /
• Density: 1.293±0.06 g/cm3(Predicted)
• PKA: 3.88±0.30(Predicted)
• CAS DataBase Reference: BOC-3-(1-PYRENYL)-L-ALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-3-(1-PYRENYL)-L-ALANINE(100442-89-5)
• EPA Substance Registry System: BOC-3-(1-PYRENYL)-L-ALANINE(100442-89-5)

Safety Data

• Hazardous Substances Data: 100442-89-5(Hazardous Substances Data)

Upstream product

• 91879-08-2 DL-1-pyrenylalanine 
• 2595-90-6 1-bromomethylpyrene 
• 24463-15-8 1-pyrenemethanol 
• 568599-06-4 diethyl 2-(1-pyrenylmethyl)-2-acetamidomalonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 87147-90-8 L-3-(1-pyrenyl)alanine 
• 91859-60-8 N-acetyl-DL-3-(1-pyrenyl)alanine 

Downstream Products

• 129149-42-4 Boc-pyrAla-Ala₂-OBzl 
• 121445-55-4 Boc-pyrAla-Glu(OBzl)4-OBzl 

Relevant articles and documents

A non-covalent strategy for the assembly of supramolecular photocurrent-generating systems

Three photocurrent-generating thin films were assembled on gold surfaces. SAM I was constructed from molecules consisting of an alkyl disulfide group linked covalently to a 12-residue helical peptide and terminated with an alanine residue containing a pyrene chromophore. SAM I served as a benchmark for multilayered films II and III in photocurrent generation experiments. Films II and III were assembled from several components that were linked noncovalently by metal-ligand complexation. Cyclic voltammetry and contact angle measurements suggest that the films consist of ordered layers with relatively few defects. Photoexcitation of SAM I by the output of a 350 nm lamp (～0.2 mW power incident on the sample) results in current generation in the range 5-10 nA/cm2. Photoexcitation of II and III yields higher current in the range 10-30 nA/cm2, representing a quantum efficiency of ～1%. The observation of comparable or higher current from noncovalently assembled multicomponent films indicates that this method of assembly may obviate the problems associated with the covalent assembly of devices from large molecules. Copyright

A pair of pyrene groups as a conformational probe for designed two α-helix polypeptides

Peptides with two α-helix segments anchored on 2,2'-bipyridyl-4,4'-dicarboxylic acid and suberic acid have been designed and synthesized.L-1-Pyrenylalanine (Pya) was introduced near the centre of each α-helical segment as a CD and fluorescent probe to detect the arrangement of the two α-helix segments.The amphiphilic α-helical 14-peptide was designed with an amino acid sequence in which the hydrophobic amino acids, Leu and Pya, are deployed in the same manner as hydrophobic amino acids in coiled-coil proteins.The synthesis was carried out by a solid-phase synthesis on Kaiser's oxime resin and solution coupling with anchors.The probing behaviour of a pair of Pya residues was examined by CD and fluorescent measurements under various conditions, e.g. in aqueous and methanolic solutions, in the presence of guanidine hydrochloride (GuHCl) and under increasing temperature.The peptides showed a highly α-helical CD pattern in the far-UV region in aqueous solution.Furthermore, they showed strong split CD peaks with positive and negative maxima at longer and shorter wavelength, respectively, at the pyrene absorption region (1La and 1Bb).These split CD signals decreased with the disruptions of the two α-helix structure by the addition of methanol, GuHCl and also with increasing temperature.On the other hand, the excimer emmission of pyrene in fluorescence was very weak in aqueous solution, but it was transiently increased while the helix-helix interaction was relaxed to some extent with the addition of methanol.These facts indicate that the two pyrene groups are forced to be in close proximity and to be in a right-handed sense between the two α-helix structures in aqueous solution; whereas, the arrangement of the pyrene groups is loosened by the destruction of the 3D structure.Thus, the pyrene probe has been demonstrated to provide significant information about the arrangement of the two α-helix segments by the simple measurements of CD and fluorescence spectra.

Photoinduced Electron Transfer on a Single α-Helical Polypeptide Chain

Electron transfer on an α-helical polypeptide carrying the sequence L-p-(dimethylamino)phenylalanine (dmaPhe)-L-alanine-L-1-pyrenylalanine (pyrAla) at the midpoint of an α-helical poly(γ-benzyl L-glutamate) chain was studied.Conformational energy calculation for the side-chain orientations predicted that only one type of orientation is allowed for both the dmaPhe and the pyrAla units.The center-to-center (edge-to-edge) distance between the two chromophores was estimated to be 13.2 (9.4) Angstroem.The fluorescence spectrum showed no exciplex emission in thepolypeptide, in contrast to the strong exciplex observed for a model tripeptide having the same dmaPhe-Ala-pyrAla sequence.The rate of electron transfer was calculated from the decay times of pyrenyl fluorescence of the polypeptide in trimethyl phosphate and in tetrahydrofuran solutions.The ket was on the order of 1E5 (s-1).The activation enthalpy was 1.4 kcal mol-1 in trimethyl phosphate and smaller than 1 kcal mol-1 in less polar solvents near room temperature.It was even smaller at lower temperatures.The activation entropy was less than -25 eu, suggesting a nonadiabatic electron transfer.In contrast to the slow electron transfer in the polypeptide, the rate constant for the model tripeptide was on the order of 1E7-1E8 (s-1) around room temperature, and the activation enthalpy was higher than that in the polypeptide case.