17224-90-7

Basic information

• Product Name: L-Phenylalanine, 4-nitro-N-[(phenylMethoxy)carbonyl]-
• Synonyms: L-Phenylalanine, 4-nitro-N-[(phenylMethoxy)carbonyl]-;4-Nitro-N-CBZ-L-phenylalanine;Benzyloxycarbonyl-p-nitro-L-phenylalanine;(S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-nitrophenyl)propanoic acid
• CAS NO: 17224-90-7
• Molecular Formula: C₁₇H₁₆N₂O₆
• Molecular Weight: 344.31874
• Mol File: 17224-90-7.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: L-Phenylalanine, 4-nitro-N-[(phenylMethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, 4-nitro-N-[(phenylMethoxy)carbonyl]-(17224-90-7)
• EPA Substance Registry System: L-Phenylalanine, 4-nitro-N-[(phenylMethoxy)carbonyl]-(17224-90-7)

Safety Data

• Hazardous Substances Data: 17224-90-7(Hazardous Substances Data)

Usage

General Description

L-Phenylalanine, 4-nitro-N-[(phenylmethoxy)carbonyl]- is a chemical compound consisting of the essential amino acid L-phenylalanine and a 4-nitro-N-[(phenylmethoxy)carbonyl] group. It is commonly used as a building block in the synthesis of peptides and proteins. L-Phenylalanine is an important amino acid involved in the production of neurotransmitters, while the 4-nitro-N-[(phenylmethoxy)carbonyl] group is a nitro-derivative often used in organic synthesis. Together, this compound has potential applications in pharmaceuticals and biotechnology as a key component in the development of novel drugs and therapeutic agents.

Upstream product

• 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 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

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

Relevant articles and documents

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).

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.

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.