5591-93-5

Upstream product

• 67-56-1 methanol 
• 2212-75-1 N₂-[(benzyloxy)carbonyl]-L-lysine 
• 2389-49-3 N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester 
• 87797-02-2 benzyloxycarbonyl-lysine 
• 2389-60-8 Z-Lys(Boc)-OH 
• 501-53-1 benzyl chloroformate 
• 14511-39-8 2(S)-2-amino-6-(benzylideneamino)hexanoic acid 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 
• 706810-26-6 N^ε-(3-methyl-2-butenyl)oxycarbonyl-L-lysine methyl ester 
• 13515-95-2 lysine methyl ester dihydrochloride 
• 648910-27-4 N^α-benzyloxycarbonyl-N^ε-(3-methyl-2-butenyl)oxycarbonyl-L-lysine methyl ester 

Downstream Products

• 148336-64-5 quinazolyl (4-N^ω)-Nα-Z-Lys-OMe 
• 103954-29-6 (2S,1'R)-N²-(Benzyloxycarbonyl)-N⁶-<1-(ethoxycarbonyl)ethyl>lysin-methylester 
• 145013-08-7 C₂₆H₄₀N₄O₈ 
• 194996-59-3 (S)-2-Benzyloxycarbonylamino-6-{2-[tert-butoxycarbonyl-(phenethylcarbamoyl-methyl)-amino]-acetylamino}-hexanoic acid methyl ester 
• 194996-63-9 (S)-2-Benzyloxycarbonylamino-6-(2-{tert-butoxycarbonyl-[(4-methoxy-benzylcarbamoyl)-methyl]-amino}-acetylamino)-hexanoic acid methyl ester 
• 194996-64-0 N-((tert-butyloxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)-N''-((5-(benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid diamide 
• 194996-61-7 (S)-2-Benzyloxycarbonylamino-6-[2-(tert-butoxycarbonyl-{[2-(4-hydroxy-phenyl)-ethylcarbamoyl]-methyl}-amino)-acetylamino]-hexanoic acid methyl ester 
• 194996-60-6 N-((tert-butyloxy)carbonyl)-N'-(2-(4-methoxyphenyl)ethyl)-N''-(5-((benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid diamide 
• 194996-62-8 N-((tert-butyloxy)carbonyl)-N'-((3-methoxyphenyl)ethyl)-N''-(5-((benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid diamide 
• 206867-00-7 N-((tert-butoxy)carbonyl)-N'-((5-(benzyloxycarbonyl)amino-5-methoxycarbonyl)pentyl)-N''-(3,4,5-trimethoxybenzyl)iminodiacetic acid diamide 
• 211745-19-6 (S)-2-Benzyloxycarbonylamino-6-(2-{[((S)-5-benzyloxycarbonylamino-5-methoxycarbonyl-pentylcarbamoyl)-methyl]-tert-butoxycarbonyl-amino}-acetylamino)-hexanoic acid methyl ester 
• 206867-09-6 N-((tert-butyloxy)carbonyl)-N'-(5-((benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid monoamide 
• 211745-36-7 N-((tert-butyloxy)carbonyl)-N'-(4-(1',4'-dioxolano)piperidino)-N''-(5-((benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid diamide 
• 401809-94-7 6-(5-benzyloxycarbonylamino-5-methoxycarbonyl-pentylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester 

Relevant academic research and scientific papers

Design and synthesis of Fmoc-SPPS-ready iodoarene amino acid pre-catalysts and their reactivity in the catalytic oxytosylation of ketones

A small suite of iodo-aryl amide containing amino acids were synthesized and assessed as catalysts for the hypervalent iodine(III) mediated α-oxytosylation of ketones. The efficiency of each catalyst was determined by comparing the relative rates of catalysis in the direct α-oxytosylation of propiophenone. In addition, these catalysts can be easily converted to congeners that are suitable for Fmoc-solid phase peptide synthesis for facile incorporation into a chiral peptide framework. This work facilitates the broader goal of our program to develop peptide-based enantioselective catalysts for hypervalent iodine chemistry.

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

The present invention relates to a conjugated compound of Formula I : Q-Z-R4 wherein Q is a TLR7 and/or TLR8 agonist and Z-R4 is a TLR2 agonist, said conjugated compound being chosen among compounds of Formula II :

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

A conjugated compound of Formula I: Q-Z—R4 wherein Q is a TLR7 and/or TLR8 agonist and Z—R4 is a TLR2 agonist, the conjugated compound being chosen among compounds of Formula II:

Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids

The present invention concerns a conjugated compound of formula Q-Z-R4 wherein Q is a TLR7 and/or TLR8 agonist and Z-R4 is a lipid covalently linked to an amino acid or peptide coupled to a polyamine group, and a process for the manufacture of said conjugated compound, as well as a complex formed between said conjugated compound and a polyanionic molecule and a pharmaceutical composition containing said conjugated compound or complex. The invention further concerns the use of said conjugated compound or complex in the treatment of infection, cancer or immune disorders or for use in vaccines.

Synthesis of crosslinking amino acids by click chemistry

Crosslinking amino acids are naturally existing protein crosslinkers. Herein, we described the synthesis of several novel bis-amino acids constituted of serine, alanine, lysine, and tyrosine with click chemistry. The Huisgen 1,3-dipolar cycloadditions bet

N-N-ACYLOXYPROPYL LYSINE METHYL ESTER- AND N,N-BIS(N- ACYLOXYPROPYL)LYSINE METHYL ESTER-TYPE COMPOUNDS AND USE THEREOF AS SURFACE-ACTIVE AGENTS WITH AN ANTIMICROBIAL ACTIVITY

The invention relates to novel compounds having an amphiphilic character (cationic, anionic, amphoteric and non-ionic), derivatives of n acyloxypropyl-type lysine amino acid according to general formula (I), which are intended to be used in the food, phar

Syntheses of amamistatin fragments and determination of their HDAC and antitumor activity

Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC50 0.24-0.56 μM). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition m

Prenyl carbamates: Preparation and deprotection

Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC6H4p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive β-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers.

One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provde the corresponding amines in good to excellent yields (63-88 percent) by using iodine in methanol followed by treatment of the resulting β-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers.

127. C-glycoside analogues of N4-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine: synthesis and conformational analysis of a cyclic C-glycopeptide

The synthesis of C-glycosidic analogues 15-22 of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine (ASn(N4GlcNAc)) possessing a reversed amide bond as an isosteric replacement of the N-glycosidic linkage is presented. The peptide cyclo(-D-Pro-Phe-Ala-CGaa-Phe-Phe-) (CGaa = C-glycosylated amino acid; 24) was prepared to demonstrate that 3-[(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D- guloheptonoyl)amino]-2-[(9H-fluoren-9-yloxycarbonyl)amino]propanoic acid (22) can be used in solid-phase peptide synthesis. The conformation of 24 was determined by NMR and molecular-dynamics (MD) techniques. Evidence is provided that the CGaa side chain interacts with the peptide backbone. The different C-glycosylated amino acids 15-21 were prepared by coupling 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo- heptonic acid (4) with diamino-acid derivatives 8-14 in 83-96% yield. The synthesis of 4 was performed from 2-(acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)tributylstannane (2) by treatment with BuLi and CO2 in 83% yield. Similarly, propyl isocyanat yielded the glycoheptonamide 7 in 52% from 2. Compound 2 was obtained from 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (1) by chlorination and addition of tributyltinlithium in 74% yield. A procedure for a multigram-scale synthesis of 1 is given.