200192-49-0

Basic information

• Product Name: N-γ-Trityl-D-asparagine
• Synonyms: N-γ-Trityl-D-asparagine;N-.GAMMA.-TRITYL-D-ASPARAGINE;(R)-2-amino-4-oxo-4-(tritylamino)butanoic acid;N-(Triphenylmethyl)-D-asparagine;(R)-4-AMino-4-oxo-2-(tritylaMino)butanoic acid;D-Asparagine, N-(triphenylmethyl)-
• CAS NO: 200192-49-0
• Molecular Formula: C23H22N2O3.H2O
• Molecular Weight: 392.453
• Mol File: 200192-49-0.mol

Chemical Properties

• Boiling Point: 641.208ºC at 760 mmHg
• Flash Point: 341.59ºC
• Appearance: /
• Density: 1.234 g/cm3
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: N-γ-Trityl-D-asparagine(CAS DataBase Reference)
• NIST Chemistry Reference: N-γ-Trityl-D-asparagine(200192-49-0)
• EPA Substance Registry System: N-γ-Trityl-D-asparagine(200192-49-0)

Safety Data

• Hazardous Substances Data: 200192-49-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-γ-Trityl-D-asparagine is used as a building block in organic synthesis for its ability to participate in various chemical reactions, contributing to the creation of complex organic molecules.
Used in Peptide Chemistry:
In peptide chemistry, N-γ-Trityl-D-asparagine is used as a protected asparagine residue, which is essential for the solid-phase peptide synthesis to produce a variety of peptides.
Used in Drug Discovery and Development:
N-γ-Trityl-D-asparagine is utilized in the field of drug discovery and development due to its stability and compatibility with numerous chemical reactions, aiding in the synthesis of potential pharmaceutical compounds.
Used in Pharmaceutical Research:
N-γ-Trityl-D-asparagine is also important in pharmaceutical research, where it helps in the development and understanding of peptide-based drugs and their mechanisms of action.

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 70-47-3 L-asparagine 
• 132388-59-1 L-Asn(Trt) 
• 132388-57-9 N-benzyloxycarbonyl-N'-trityl-L-asparagine 

Downstream Products

• 132388-68-2 N^α-tert-butoxycarbonyl-N^ω-triphenylmethyl-L-asparagine 
• 1542166-89-1 (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid 
• 1542166-90-4 (S)-tert-butyl 4-((((S)-1-amino-1,4-dioxo-4-(tritylamino)butan-2-yl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1542166-91-5 (S)-tert-butyl 4-((((S)-1-cyano-3-oxo-3-(tritylamino)propyl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1542166-92-6 (S)-tert-butyl 4-((((S)-1-amino-1-(hydroxyimino)-4-oxo-4-(tritylamino)butan-2-yl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1542166-93-7 4-tert-butyl 6-ethyl 2-((S)-1-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-3-oxo-3-(tritylamino)propyl)-5-methylpyrimidine-4,6-dicarboxylate 
• 1542166-86-8 C₃₄H₄₃N₅O₄ 
• 1542166-94-8 4-tert-butyl 6-ethyl 2-((S)-1-((tert-butyloxycarbonyl)(((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-3-oxo-3-(tritylamino)propyl)-5-methylpyrimidine-4,6-dicarboxylate 
• 1542166-95-9 (S)-tert-butyl 4-(((tert-butyloxycarbonyl)((S)-1-(4-(tert-butyloxycarbonyl)-6-((tertbutyloxycarbonyl)amino)-5-methylpyrimidin-2-yl)-3-oxo-3-(tritylamino)propyl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1542166-96-0 tert-butyl 2-((5S,8S)-6-(tert-butyloxycarbonyl)-8-(hydroxymethyl)-12,12-dimethyl-3,10-dioxo-1,1,1-triphenyl-11-oxa-2,6,9-triazatridecan-5-yl)-6-((tert-butyloxycarbonyl)amino)-5-methylpyrimidine-4-carboxylate 
• 1542166-97-1 (S)-3-((tert-butyloxycarbonyl)((S)-1-(4-(tert-butyloxycarbonyl)-6-((tertbutyloxycarbonyl)amino)-5-methylpyrimidin-2-yl)-3-oxo-3-(tritylamino)propyl)amino)-2-((tert-butyloxycarbonyl)amino)propanoic acid 
• 1542166-98-2 tert-butyl 2-((5S,8S)-6-(tert-butyloxycarbonyl)-8-carbamoyl-12,12-dimethyl-3,10-dioxo-1,1,1-triphenyl-11-oxa-2,6,9-triazatridecan-5-yl)-6-((tert-butyloxycarbonyl)amino)-5-methylpyrimidine-4-carboxylate 
• 1542167-05-4 4-(tert-butyl) 6-ethyl 2-((S)-1-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-3-oxo-3-(tritylamino)propyl)pyrimidine-4,6-dicarboxylate 
• 1542167-06-5 4-(tert-butyl) 6-ethyl 2-((S)-1-((tert-butyloxycarbonyl)(((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-3-oxo-3-(tritylamino)propyl)pyrimidine-4,6-dicarboxylate 

Relevant articles and documents

Cystobactamid 507: Concise Synthesis, Mode of Action, and Optimization toward More Potent Antibiotics

Lack of new antibiotics and increasing antimicrobial resistance are among the main concerns of healthcare communities nowadays, and these concerns necessitate the search for novel antibacterial agents. Recently, we discovered the cystobactamids—a novel natural class of antibiotics with broad-spectrum antibacterial activity. In this work, we describe 1) a concise total synthesis of cystobactamid 507, 2) the identification of the bioactive conformation using noncovalently bonded rigid analogues, and 3) the first structure–activity relationship (SAR) study for cystobactamid 507 leading to new analogues with high metabolic stability, superior topoisomerase IIA inhibition, antibacterial activity and, importantly, stability toward the resistant factor AlbD. Deeper insight into the mode of action revealed that the cystobactamids employ DNA minor-groove binding as part of the drug–target interaction without showing significant intercalation. By designing a new analogue of cystobactamid 919-2, we finally demonstrated that these findings could be further exploited to obtain more potent hexapeptides against Gram-negative bacteria.

A mild removal of Fmoc group using sodium azide

A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected Nα-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis. Graphical Abstract: [Figure not available: see fulltext.]

N-METHYL AMINO ACIDS

The present invention relates to a compound of formula (I) or (II), processes for preparing them, peptides including them and kits involving them.

A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan

(graph presented) R = CH2(3-indolyl) tryptophan R = CH2CONH2 asparagine R = CH2(2-imidazolyl) histidine R = CH2CH2CH2(guanidyl) arginine N-Methyl amino acid residues in peptides

Protected amino acids and process for the preparation thereof

Compounds of the formula I, STR1 in which 'R1 is an amino protective group, and n stands for 1 or 2, R1 denotes hydrogen or an amino protective group, R2 denotes hydrogen or a carboxyl protective group and R3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R2 stands for hydrogen, are described. These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.

Protection of carboxamide functions by the trityl residue. Application to peptide synthesis

Carboxamide functions may be tritylated by an acid-catalyzed reaction with triphenylmethanol and acetic anhydride in glacial acetic acid. The ω-trityl group of asparagine and glutamine is cleavable by TFA, but stable to strong mineral acids in aqueous solution, as well as to nucleophiles and bases. In peptide syntheses, it is ideally suited for combination with side-chain protections of the t.butyl-type.