127095-97-0 Usage
Description
BOC-3,4-DIMETHOXY-L-PHENYLALANINE, with the molecular formula C17H23NO5, is an amino acid derivative and a specific variant of phenylalanine. This chemical compound is characterized by the presence of a tert-butyloxycarbonyl (BOC) protecting group and two methoxy substituents on the aromatic ring. It plays a significant role in organic synthesis and pharmaceutical research, serving as a versatile building block for the creation of bioactive compounds and pharmaceuticals.
Uses
Used in Organic Synthesis:
BOC-3,4-DIMETHOXY-L-PHENYLALANINE is used as a key intermediate in organic synthesis for the preparation of a variety of complex organic molecules. Its unique structural features allow for selective reactions and modifications, facilitating the synthesis of target compounds with specific biological activities.
Used in Pharmaceutical Research:
In pharmaceutical research, BOC-3,4-DIMETHOXY-L-PHENYLALANINE is utilized as a building block for the development of new drugs. Its incorporation into drug molecules can enhance their pharmacological properties, such as potency, selectivity, and bioavailability, leading to more effective treatments for various diseases.
Used as a Precursor in Peptide Synthesis:
BOC-3,4-DIMETHOXY-L-PHENYLALANINE is commonly used as a precursor in the synthesis of peptides and peptidomimetics. Its presence in peptide sequences can impart specific biological functions, such as enzyme inhibition or receptor modulation, which are crucial for the therapeutic effects of peptide-based drugs.
Used in Drug Discovery:
BOC-3,4-DIMETHOXY-L-PHENYLALANINE has potential applications in the field of drug discovery, where it can be employed to explore novel chemical space and identify new lead compounds with promising pharmacological profiles. Its unique structural features and reactivity make it a valuable tool for the design and optimization of drug candidates.
Used in Medicinal Chemistry:
In medicinal chemistry, BOC-3,4-DIMETHOXY-L-PHENYLALANINE is used to study the structure-activity relationships of bioactive molecules. By incorporating this compound into various chemical scaffolds, researchers can gain insights into the molecular interactions that govern the biological activity of drug molecules, guiding the design of more effective therapeutic agents.
Check Digit Verification of cas no
The CAS Registry Mumber 127095-97-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,7,0,9 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 127095-97:
(8*1)+(7*2)+(6*7)+(5*0)+(4*9)+(3*5)+(2*9)+(1*7)=140
140 % 10 = 0
So 127095-97-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H23NO6/c1-16(2,3)23-15(20)17-11(14(18)19)8-10-6-7-12(21-4)13(9-10)22-5/h6-7,9,11H,8H2,1-5H3,(H,17,20)(H,18,19)/t11-/m0/s1
127095-97-0Relevant articles and documents
Photocyclization of Tetra- and Pentapeptides Containing Adamantylphthalimide and Phenylalanines: Reaction Efficiency and Diastereoselectivity
Sohora, Margareta,Vazdar, Mario,Sovi?, Irena,Mlinari?-Majerski, Kata,Basari?, Nikola
, p. 14905 - 14922 (2019/01/04)
A series of tetrapeptides and pentapeptides was synthesized bearing a phthalimide chromophore at the N-terminus. The C-terminus of the peptides was strategically substituted with an amino acid, Phe, Phe(OMe), or Phe(OMe)2 characterized by different oxidation potentials. The photochemical reactivity of the peptides was investigated by preparative irradiation and isolation of photoproducts, as well as with laser flash photolysis. Upon photoexcitation, the peptides undergo photoinduced electron transfer (PET) and decarboxylation, followed by diastereoselective cyclization with the retention of configuration for tetrapeptides or inversion of configuration for pentapeptides. Molecular dynamics (MD) simulations and NOE experiments enabled assignment of the stereochemistry of the cyclic peptides. MD simulations of the linear peptides disclosed conformational reasons for the observed diastereoselectivity, being due to the peptide backbone spatial orientation imposed by the Phe amino acids. The photochemical efficiency for the decarboxylation and cyclization is not dependent on the peptide length, but it depends on the oxidation potential of the amino acid at the C-terminus. The results described herein are particularly important for the rational design of efficient photochemical reactions for the preparation of cyclic peptides with the desired selectivity.
Synthesis of tetrahydroisoquinoline-based pseudopeptides and their characterization as suitable reverse turn mimetics
Lesma, Giordano,Meschini, Elisa,Recca, Teresa,Sacchetti, Alessandro,Silvani, Alessandra
, p. 5567 - 5578 (2007/12/30)
New peptidomimetics containing the Tic moiety were synthesized in enantiomerically pure form and their conformational features were studied by NMR, IR, and molecular modeling techniques. The presence of a reverse turn conformation was observed in all the
Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations
García, Eva,Arrasate, Sonia,Ardeo, Ainhoa,Lete, Esther,Sotomayor, Nuria
, p. 1511 - 1513 (2007/10/03)
Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3·OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%).
