45895-90-7

Upstream product

• 75-44-5 phosgene 
• 73-32-5 DL-isoleucine 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 73-32-5 L-isoleucine 
• 319-78-8 isoleucine 
• 59483-84-0 bis(pentafluorophenyl)carbonate 
• 7497-12-3 bis(2,4-dinitrophenyl) carbonate 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 67-66-3 chloroform 
• 7483-92-3 TMS-DL-Ile-OTMS 
• 7483-92-3 TMS-DL-(allo-Ile)-OTMS 

Downstream Products

• 54745-13-0 (S)-4-(S)-sec-butyl-3-(2-nitro-phenylsulfanyl)-oxazolidine-2,5-dione 
• 462-60-2 N-carbamoylglycine 
• 41017-96-3 L-isoleucyl-L-valine 
• 129288-41-1 (S)-4-((S)-sec-Butyl)-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 868-28-0 isoleucyl‐glycine 
• 73-32-5 L-isoleucine 
• 54745-25-4 NPS-Ile-Glyc 

Relevant academic research and scientific papers

METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE

PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

METHOD OF SYNTHESIZING N-CARBOXYANHYDRIDE USING FLOW REACTOR

PROBLEM TO BE SOLVED: To provide a synthesis method that allows high-yield continuous production of a compound of interest in synthesis and production of N-carboxyanhydride (NCA) and the like using a flow reactor. SOLUTION: In a synthesis method using a flow reactor 100, a basic solution adjusted in advance to a pH of 7-14 becomes acidic with a pH of 0-7, or an acidic solution adjusted in advance to a pH of 0-7 becomes basic with a pH of 7-14, within 60 seconds after the start of mixture of at least two ingredient solutions. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor

Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.

Revisiting the Juliá-Colonna enantioselective epoxidation: Supramolecular catalysis in water

We describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-l-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the α-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.

Multi-responsive polypeptide hydrogels derived from: N -carboxyanhydride terpolymerizations for delivery of nonsteroidal anti-inflammatory drugs

A polypeptide-based hydrogel system, when prepared from a diblock polymer with a ternary copolypeptide as one block, exhibited thermo-, mechano- and enzyme-responsive properties, which enabled the encapsulation of naproxen (Npx) during the sol-gel transition and its release in the gel state. Statistical terpolymerizations of l-alanine (Ala), glycine (Gly) and l-isoleucine (Ile) NCAs at a 1:1:1 feed ratio initiated by monomethoxy monoamino-terminated poly(ethylene glycol) afforded a series of methoxy poly(ethylene glycol)-block-poly(l-alanine-co-glycine-co-l-isoleucine) (mPEG-b-P(A-G-I)) block polymers. β-Sheets were the dominant secondary structures within the polypeptide segments, which facilitated a heat-induced sol-to-gel transition, resulting from the supramolecular assembly of β-sheets into nanofibrils. Deconstruction of the three-dimensional networks by mechanical force (sonication) triggered the reverse gel-to-sol transition. Certain enzymes could accelerate the breakdown of the hydrogel, as determined by in vitro gel weight loss profiles. The hydrogels were able to encapsulate and release Npx over 6 days, demonstrating the potential application of these polypeptide hydrogels as an injectable local delivery system for small molecule drugs.

PROCESS FOR PRODUCING AMINO ACID N-CARBOXYANHYDRIDE

The present invention provides a process for producing an amino acid N-carboxyanhydride, which comprises reacting an amino acid or a derivative thereof with a compound represented by the following formula (1): wherein R1 and R2 represent the same or different electron-withdrawing substituents and each independently are an optionally substituted acyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted perfluoroalkyl group, an optionally substituted perchloroalkyl group, a cyano group, a halogen atom, or a nitro group; and a and b are the same or different and each are an integer of 1-5.

Friedel-Crafts α-Aminoacylation of Alkylbenzene with a Chiral N-Carboxy-α-amino Acid Anhydride without Loss of Chirality

A Friedel-Crafts-type α-aminoacylation of alkylbenzene with N-carboxy anhydrides of five L-α-amino acids was developed.Five new α-aminoalkyl p-methylphenyl ketones and other α-aminoalkyl aryl ketones were obtained and isolated as free bases or hydrochloride salts.The chiralities of the original L-α-amino acids were retained during this acylation.

ENANTIOMERIC QUANTIFICATIONS OF AMINO ACIDS THROUGH THEIR Nα-ACYL AMIDES BY GAS CHROMATOGRAPHY.

Apparent separation of 1.1 or higher on Chiralsil Val III can be obtained for Nα-acyl N-alkyl aminoacid amides allowing the use of short capillary gas chromatographic columns.A clean derivatization protocol without racemization is described, proceding through the NCA derivatives that are prepared from "in situ" silylated amino acids with trimethylsilyl cyanide.

SYNTHETIC ENZYMES-4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM: INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS.

The asymmetric epoxidation of chalcone and other electron-poor olefins in a triphase system (water-organic solvent-polyaminoacid) affords optically active oxiranes.The influence of the molecular structure of catalysts and of their secondary conformation on the enantioselectivity of the reaction has also been examined.

2-Alkoxy-5(4H)-oxazolones from N-alkoxycarbonylamino acids and their implication in carbodiimide-mediated reactions in peptide synthesis

Reaction of N-ethyl,N'-(γ-dimethylaminopropyl)-carbodiimide*HCl with one equiv. of N-tert-butoxycarbonyl-L-valine (3a) in dichloromethane at 23 degC gives, besides the symmetrical anhydride (5a), the optically pure 2-tert-butoxy-4-isopropyl-5(4H)-oxazolone (4a) which can be obtained in 50percent yield under selected conditions.The 2-benzyloxycarbonyl-4-isopropyl-5(4H)-oxazolone (4b) is similarly obtainable from N-benzyloxycarbonyl-L-valine (3b).Anhydrous acid converts 4a to the oxazolidinedione.Simple preparations of the N-carboxyanhydrides of valine and isoleucine have been devised from these reactions.Compound 4 reacts with 3 to give 5.Compound 4 reacts with an amino acid ester to give the optically pure peptide even in the presence of salts, but partial racemization occurs for reactions in the presence of a tertiary amine.Evidence for the implication of 2-alkoxy-5(4H)-oxazolones in the couplings of N-alkoxycarbonylamino acids is presented.Compound 4a has been isolated in 6-11percent yield from carbodiimide-mediated reactions of 3a with itself or amino acid methyl esters which have been terminated before completion.