17224-90-7

Usage

Uses

Used in Pharmaceutical Industry:
L-Phenylalanine, 4-nitro-N-[(phenylmethoxy)carbonyl]is used as a key component in the development of novel drugs and therapeutic agents due to its role as a building block in peptide and protein synthesis.
Used in Biotechnology Industry:
L-Phenylalanine, 4-nitro-N-[(phenylmethoxy)carbonyl]is used as a crucial element in the creation of new biotechnological applications, leveraging its properties in peptide and protein synthesis for various therapeutic purposes.

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 501-53-1 benzyl chloroformate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 147065-06-3 L-nitrophenylalanine hydrochloride 

Downstream Products

• 1224923-31-2 C₁₇H₁₇N₃O₂ 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 228261-84-5 C₁₇H₁₈N₂O₄ 
• 869882-71-3 C₂₁H₂₄N₂O₆ 
• 686777-00-4 1,4,7-tris(tert-butylacetate)-1,4,7,10-tetraazacyclododecane-10-N-α-carbobenzyloxy-p-bromoacetylamide-L-phenylalanine benzyl ester 
• 686776-99-8 N-α-carbobenzyloxy-p-bromoacetylamide-L-phenylalanine benzyl ester 
• 686776-98-7 N-α-carbobenzyloxy-p-amino-L-phenylalanine benzyl ester 
• 686776-97-6 N-α-carbobenzyloxy-p-nitro-L-phenylalanine benzyl ester 
• 126689-35-8 [(S)-1-[N',N'-Bis-(2-chloro-ethyl)-hydrazinocarbonyl]-2-(4-nitro-phenyl)-ethyl]-carbamic acid benzyl ester 
• 126689-36-9 (S)-2-Amino-3-(4-nitro-phenyl)-propionic acid N',N'-bis-(2-chloro-ethyl)-hydrazide; hydrobromide 

Relevant academic research and scientific papers

Aza-cycloisodityrosine analogue of RA-VII, an antitumor bicyclic hexapeptide

An aza-cycloisodityrosine analogue of RA-VII, 3, was designed and synthesized. The key aza-cycloisodityrosine unit was prepared by copper(II)-acetate-mediated intramolecular phenylamine/arylboronic acid coupling of dipeptide followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with EDC·HCl and HOOBt under dilute conditions gave 3. Analogue 3 showed significant cytotoxic activity against human promyelocytic leukemia HL-60 cells and human colon carcinoma HCT-116 cells, but its activity was weaker than that of parent peptide RA-VII (1).

Sulfur(VI) Fluoride Exchange (SuFEx)-Enabled High-Throughput Medicinal Chemistry

Optimization of small-molecule probes or drugs is a synthetically lengthy, challenging, and resource-intensive process. Lack of automation and reliance on skilled medicinal chemists is cumbersome in both academic and industrial settings. Here, we demonstr

Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group

In order to deprotect N-carbobenzoxy-l-aminoacids (Cbz-AA) and related compounds, a series of microorganisms was selected from soil by enrichment cultures with Cbz-l-Glu as sole nitrogen source. A lyophilized whole-cell preparation of two Arthrobacter sp. strains grown on Cbz-Glu or Cbz-Gly exhibited a high cleavage activity. The conditions of hydrolysis have been optimized and a quantitative enantioselective deprotection of several Cbz-dl-amino acids was obtained, as well as the deprotection of N-carbamoylester derivatives of several synthetic amino compounds. The preparation of Cbz-d-allylglycine and l-allylglycine in high yield and high optical purity is described as an application of this method.

Design and evaluation of Trypanosoma brucei metacaspase inhibitors

Metacaspase (MCA) is an important enzyme in Trypanosoma brucei, absent from humans and differing significantly from the orthologous human caspases. Therefore MCA constitutes a new attractive drug target for antiparasitic chemotherapeutics, which needs further characterization to support the discovery of innovative drug candidates. A first series of inhibitors has been prepared on the basis of known substrate specificity and the predicted catalytic mechanism of the enzyme. In this Letter we present the first inhibitors of TbMCA2 with low micromolar enzymatic and antiparasitic activity in vitro combined with low cytotoxicity.

Compounds and Compositions as Channel Activating Protease Inhibitors

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

PREPARATION OF POLYMER CONJUGATES OF THERAPEUTIC, AGRICULTURAL, AND FOOD ADDITIVE COMPOUNDS

Disclosed is a process for preparing polymer conjugates of agricultural, therapeutic, and food additive compounds using Mitsunobu conditions.

Multimeric VLA-4 antagonists comprising polymer moieties

Disclosed are conjugates which bind VLA-4. Certain of these conjugates also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such conjugates are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The conjugates can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

IMIDAZOLONE PHENYLALANINE DERIVATIVES AS VLA-4 ANTAGONISTS

Disclosed are compounds of the f ormula : and the pharmaceutically acceptable salts thereof wherein the variables A, n, R5, R21-R24 and Q are defined herein. These compounds bind VLA-4. Certain of these compound also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

Pyrimidine hydantoin analogues which inhibit leukocyte adhesion mediated by VLA-4

Disclosed are compounds which bind VLA-4 and/or LPAM-1. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4 and/or LPAM-1. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

Solid-Phase Synthesis of DOTA-Peptides

A general synthetic route to two DOTA-linked N-Fmoc amino acids (DOTA-F and DOTA-K) is described that allows insertion of DOTA at any endo-position within a peptide sequence. Three model pentapeptides were prepared to test the general utility of these derivatives in solid-phase peptide synthesis. Both DOTA derivatives reacted smoothly by means of standard HBTU activation chemistry to the point of insertion of the DOTA amino acid, but extension of the peptide chain beyond the DOTA-amino acid insertion required the use of pre-activated C-pentafluorophenyl ester N-α-Fmoc amino acids. Three Gal-80 binding peptides (12-mers) were then prepared by using this methodology with DOTA positioned either at the N terminus or at one of two different internal positions;the binding of the resulting GdDOTA-12-mers to Gal-80 were compared. The methodology described here allows versatile, controlled introduction of DOTA into any location within a peptide sequence. This provides a potential method for the screening of libraries of DOTA-linked peptides for optimal targeting properties.