1956434-65-3 Usage
Description
N-Fmoc-7-fluoro-L-tryptophan is a chemical compound that serves as a protected form of 7-fluoro-L-tryptophan, an amino acid derivative. It is characterized by the presence of a fluorine atom at the 7th position of the tryptophan molecule and is protected by the 9-fluorenylmethoxycarbonyl (Fmoc) group, which is commonly used in peptide synthesis to prevent unwanted side reactions.
Uses
Used in Pharmaceutical Industry:
N-Fmoc-7-fluoro-L-tryptophan is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting the tryptophan indole-lyase enzyme from E. coli. This enzyme is involved in the breakdown of tryptophan, and its inhibition can have therapeutic applications in conditions where tryptophan metabolism is dysregulated.
Used in Research and Development:
In the field of research and development, N-Fmoc-7-fluoro-L-tryptophan is utilized as a building block for the synthesis of novel peptides and peptidomimetics. The Fmoc protection group allows for the stepwise assembly of complex peptide structures, and the 7-fluoro substitution can impart unique properties to the resulting peptides, making them valuable tools for studying biological processes and developing new therapeutic agents.
Used in Drug Design:
N-Fmoc-7-fluoro-L-tryptophan is also used in drug design to create analogs of natural peptides and proteins with altered biological activities. The fluorine atom can modulate the binding affinity, stability, and selectivity of the peptide for its target, potentially leading to improved drug candidates with enhanced efficacy and reduced side effects.
Check Digit Verification of cas no
The CAS Registry Mumber 1956434-65-3 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,9,5,6,4,3 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1956434-65:
(9*1)+(8*9)+(7*5)+(6*6)+(5*4)+(4*3)+(3*4)+(2*6)+(1*5)=213
213 % 10 = 3
So 1956434-65-3 is a valid CAS Registry Number.
1956434-65-3Relevant articles and documents
Tuning the Biological Activity of RGD Peptides with Halotryptophans ?
Kemker, Isabell,Schr?der, David C.,Feiner, Rebecca C.,Müller, Kristian M.,Marion, Antoine,Sewald, Norbert
, p. 586 - 601 (2021/01/14)
An array of l- and d-halotryptophans with different substituents at the indole moiety was synthesized employing either enzymatic halogenation by halogenases or incorporation of haloindoles using tryptophan synthase. Introduction of these Trp derivatives into RGD peptides as a benchmark system was performed to investigate their influence on bioactivity. Halotryptophan-containing RGD peptides display increased affinity toward integrin αvβ3 and enhanced selectivity over integrin α5β1. In addition, bromotryptophan was exploited as a platform for late-stage diversification by Suzuki-Miyaura cross-coupling (SMC), resulting in new-to-nature biaryl motifs. These peptides show enhanced affinity toward αvβ3, good affinity to αvβ8, and remarkable selectivity over α5β1 and αIIbβ3 while featuring fluorogenic properties. Their feasibility as a probe was demonstrated in vitro. Extensive molecular dynamics simulations were undertaken to elucidate NMR and high-performance liquid chromatography (HPLC) data for these late-stage diversified cyclic RGD peptides and to further characterize their conformational preferences.
