125342-48-5

Basic information

• Product Name: DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-
• Synonyms: DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-;Boc-DL-norleucine
• CAS NO: 125342-48-5
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231
• Mol File: 125342-48-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-(125342-48-5)
• EPA Substance Registry System: DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-(125342-48-5)

Safety Data

• Hazardous Substances Data: 125342-48-5(Hazardous Substances Data)

Usage

General Description

DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]- is a chemical compound that is derived from norleucine, an essential amino acid. It is commonly used in the production of peptides and proteins, as well as in pharmaceuticals and biochemical research. The compound is known for its ability to improve the stability and solubility of peptides and proteins, making it an important additive in various biotechnological applications. Additionally, DL-Norleucine, N-[(1,1-dimethylethoxy)carbonyl]- is also used in the synthesis of new and modified amino acids, and it is considered to be a valuable tool for researchers in the field of biochemistry and molecular biology.

Upstream product

• 109-65-9 1-bromo-butane 
• 4530-20-5 BOC-glycine 
• 616-06-8 2-amino-hexanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 70288-84-5 2-aminohexanoic acid (hydrochloride) 

Downstream Products

• 125342-49-6 [1-(2-Benzyloxycarbonylamino-ethylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester 
• 439287-52-2 (+/-)-2-(tert-butoxycarbonyl)-amino-N-[(2,6-dimethyl)phenyl]hexanamide 
• 367258-50-2 {1-[({[(dimethylcarbamoyl-phenyl-methyl)-carbamoyl]-methyl}-carbamoyl)-hydroxy-methyl]-pentyl}-carbamic acid tert-butyl ester 
• 104062-70-6 (1-formyl-pentyl)-carbamic acid tert-butyl ester 
• 120369-42-8 L-N-Boc-norleucine benzylamide 

Relevant articles and documents

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.

BENZOTHIA(DI)AZEPINE COMPOUNDS AND THEIR USE AS BILE ACID MODULATORS

The invention relates to 1,5-benzothiazepine and 1,2,5-benzothiadiazepine derivatives of formula (I). These compounds are bile acid modulators having apical sodium-dependent bile acid transporter (ASBT) and/or liver bile acid transport (LBAT) inhibitory activity. The invention also relates to pharmaceutical compositions comprising these compounds and to the use of these compounds in the treatment of cardiovascular diseases, fatty acid metabolism and glucose utilization disorders, gastrointestinal diseases and liver diseases.

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.