2483-48-9

Usage

Uses

Used in Biochemistry and Pharmaceutical Research:
(+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester is used as an intermediate in the development and synthesis of various peptides for therapeutic and research purposes. Its role in peptide synthesis is crucial due to its protected carboxyl and amino groups, which enable selective deprotection and further modification of peptides.
Used in Solid-Phase Peptide Synthesis:
In the field of solid-phase peptide synthesis, (+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester is used as a building block for the production of polypeptides. Its protected carboxyl groups facilitate the stepwise assembly of peptide chains, making it an essential component in this synthesis process.
Used in the Production of Polypeptides:
(+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester is also utilized in the production of polypeptides, which are short chains of amino acids. Its protected functional groups allow for the controlled synthesis of these polypeptides, which can be used in various applications, including drug development and research.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 186581-53-3 diazomethane 
• 2483-46-7 Boc-Lys(Boc)-OH 
• 657-27-2 L-Lysine hydrochloride 
• 687-64-9 L-lysine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13515-95-2 lysine methyl ester dihydrochloride 
• 67-56-1 methanol 
• 56-87-1 L-lysine 
• 100-36-7 N,N-diethylethylenediamine 
• 588719-15-7 N-benzyloxycarbonyl-N-tert-butyloxycarbonyl-ω-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}lysine methyl ester 
• 74-88-4 methyl iodide 
• 26348-68-5 N-(benzyloxycarbonyl)lysine methyl ester hydrochloride 
• 588719-10-2 N-benzyloxycarbonyl-ω-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}lysine methyl ester 

Downstream Products

• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 158362-66-4 (2R,5S)-1-aza-3-oxa-9-oxo-2-phenylbicyclo[4.3.0]nonane 
• 158362-68-6 (3R,8aS)-3-Phenyl-6-phenylselanyl-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-5-one 
• 158362-67-5 (+)-(2R,5S)-1-aza-3-oxa-9-oxo-2-phenyl-8,8-bis(phenylselenenyl)bicyclo[4.3.0]nonane 
• 687-64-9 L-lysine methyl ester 
• 819871-13-1 [5-tert-butoxycarbonylamino-5-(1-methyl-2-phenylethylcarbamoyl)pentyl]carbamic acid tert-butyl ester 
• 1374137-98-0 tert-butyl [(5S)-5-[(tert-butoxycarbonyl)amino]-6-{[tert-butyl(diphenyl)silyl]oxy}hexyl]carbamate 
• 1374138-11-0 N-[(2R,5S)-5-{[(4-aminophenyl)sulfonyl](3-methylbutyl)amino}-2-fluoro-6-hydroxy-hexyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374138-12-1 N-[(2S,5S)-5-{[(4-aminophenyl)sulfonyl](3-methylbutyl)amino}-2-fluoro-6-hydroxy-hexyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374137-87-7 N-[(5S)-5-{[(4-aminophenyl)sulfonyl](3-methylbutyl)amino}-2-fluoro-6-hydroxy-hexyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374138-10-9 N-[(5S)-2-fluoro-6-hydroxy-5-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}hexyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374138-09-6 N-[(5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-2-fluoro-5-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}hexyl]-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374138-08-5 N-{(5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-2-fluoro-5-[(3-methylbutyl)amino]hexyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide 
• 1374138-07-4 benzyl [(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-5-fluoro-6-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}hexan-2-yl](3-methylbutyl)carbamate 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF LISDEXAMFETAMINE AND RELATED DERIVATIVES

The present invention is directed to processes for the preparation of lisdexamfetamine and related derivatives, wherein the processes comprise coupling to racemic or enantiomerically enriched amphetamine and wherein the resulting product is advantageously enantiomerically or diastereomerically enriched in the desired stereoisomer.

1,3,4-OXADIAZOLE AND THIADIAZOLE COMPOUNDS AS IMMUNOMODULATORS

The present invention relates to 1,3,4-oxadiazole and thiadiazole compounds of formula (I) and their use to inhibit the programmed cell death 1 (PD-1) signaling pathway and/or for treatment of disorders by inhibiting an immunosuppressive signal induced by

HIV PROTEASE INHIBITORS

Compounds of Formula I are disclosed wherein R1, R2, R3A, R3B, R4A, R4B, R5A, R5B, R6A, R6B, R7, R8 and R9 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

Universal peptidomimetics

This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.

HIV PROTEASE INHIBITORS

Compounds of Formula I are disclosed: (I), wherein XA, k, R1, R2, R3, R4, R5, R5A, R6, R6A, R7 and R8 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

A facile access to pyrroles from amino acids via an aza-Wacker cyclization

(Chemical Equation Presented) A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf) 2. A series of pyrroles were obtained by this method under mild conditions.

General synthesis of pyrroloquinolizidines: Synthesis of an unnatural homologue of the pyrroloindolizidine myrmicarin alkaloid 215B

A general synthesis approach to pyrroloquinolizidines (3,4,5,5a,6,7,8- heptahydropyrrolo[2,1,5-de]-quinolizines) via a muenchnone 1,3-dipolar cycloaddition is reported. The approach was applied to the synthesis of an unnatural pyrroloquinolizidine homologue of myrmicarin 215B.

Development of a temporary marker for peptides

3-[(N,N-Dimethylaminophenyl)-4′-diazenyl]benzoic acid was coupled with several amino acid esters and the product acylated further with Boc. The material thus obtained was then submitted to cleavage by electrolysis and nucleophilic attack in order to evaluate the possibility of using this chromophore as a temporary marker.

Calixarene amino acids; building blocks for calixarene peptides and peptide-dendrimers

A modular strategy towards receptor macromolecules is presented, which combines synthetically diverse peptide synthesis with highly functional calixarene chemistry. The design and synthesis of calix[4]arene amino acids 1a-f, calix-lysines, is described, which were used as construction blocks to assemble nanoscale, multivalent entities - calix-peptides 2 and calix-peptide-dendrimers 3.

Diels-Alder reactions of 6-substituted 1-(p-nitrobenzoyl)-5,6-dihydro-2-pyridinones

The first examples of Diels-Alder cycloaddition reactions of 6-substituted 1-(p-nitrobenzoyl)-5,6-dihydro-2-pyridinones are described. This reaction benefits from the fact that the diene adopts an endo orientation trans to the axial substituent at C-6 due to A1,3 allylic type strain with the N-PNB protecting group.