132388-58-0

Basic information

• Product Name: N'-Trityl-L-asparagine
• Synonyms: L-ASPARAGINE (TRITYL);H-ASN(TRT)-OH;ASPARAGINE(TRT);N-BETA-TRITYL-L-ASPARAGINE;N-(TRIPHENYLMETHYL)-L-ASPARAGINE;N-γ-Trityl-L-asparagine;H-L-Asn(Trt)-OH;N-.GAMMA.-TRITYL-L-ASPARAGINE
• CAS NO: 132388-58-0
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.43
• Product Categories: Amino Acids Derivatives;Asparagine [Asn, N];Amino Acids and Derivatives
• Mol File: 132388-58-0.mol

Chemical Properties

• Boiling Point: 641.2 °C at 760 mmHg
• Flash Point: 341.6 °C
• Appearance: White/Powder
• Density: 1.234 g/cm³
• Vapor Pressure: 2.56E-17mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: -20°C
• PKA: 2.41±0.10(Predicted)
• CAS DataBase Reference: N'-Trityl-L-asparagine(CAS DataBase Reference)
• NIST Chemistry Reference: N'-Trityl-L-asparagine(132388-58-0)
• EPA Substance Registry System: N'-Trityl-L-asparagine(132388-58-0)

Safety Data

• Hazardous Substances Data: 132388-58-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N'-Trityl-L-asparagine is used as a building block for the synthesis of complex molecules and pharmaceutical compounds. Its unique structure allows for the creation of novel drugs with potential therapeutic applications.
Used in Peptide Synthesis:
N'-Trityl-L-asparagine is used as a protected amino acid in peptide synthesis. The trityl group provides protection to the amino group, preventing unwanted side reactions during the synthesis process and ensuring the correct formation of peptide bonds.
Used in Research and Development:
N'-Trityl-L-asparagine is used as a research tool in the study of protein structure, function, and interactions. Its unique properties allow scientists to investigate the role of specific amino acids in protein folding, stability, and binding.
Used in Preparation of Islet Amyloid Polypeptide:
N'-Trityl-L-asparagine is used in the preparation of islet amyloid polypeptide, a hormone produced by the pancreas that plays a crucial role in regulating blood sugar levels. N'-Trityl-L-asparagine aids in the synthesis and purification of this peptide, contributing to research on diabetes and related conditions.

InChI:InChI=1/C23H22N2O3/c24-20(22(27)28)16-21(26)25-23(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15,20H,16,24H2,(H,25,26)(H,27,28)/t20-/m0/s1

Upstream product

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

Downstream Products

• 132388-68-2 N^α-tert-butoxycarbonyl-N^ω-triphenylmethyl-L-asparagine 
• 197245-33-3 Bsmoc-Asn(Trt)-OH 
• 132388-57-9 N-benzyloxycarbonyl-N'-trityl-L-asparagine 
• 941296-84-0 N^α-nosyl-N^β-trityl-L-asparagine 
• 1209480-95-4 NVOC-Asn(Trt)-OH 
• 1221251-52-0 C₅₈H₇₄N₆O₁₀ 
• 1221251-49-5 C₅₅H₆₈N₆O₁₀ 
• 1221251-44-0 Ac-W(Boc)-S(t-Bu)-N(Trt)-L 
• 1283599-85-8 C₄₀H₂₉N₃O₉ 
• 1283599-25-6 C₃₇H₂₄N₂O₈ 
• 1283599-43-8 C₃₇H₂₆N₂O₉ 
• 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 

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.