172846-56-9

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2389-49-3 N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 67-56-1 methanol 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 74-88-4 methyl iodide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 186581-53-3 diazomethane 

Downstream Products

• 3017-32-1 (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate 
• 687-64-9 L-lysine methyl ester 
• 105047-45-8 Fmoc-Lys-OH 
• 849752-43-8 2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-hexanoic acid 
• 849752-40-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-hexanoic acid methyl ester 

Relevant academic research and scientific papers

Modular Solid-Phase Synthesis of Antiprotozoal Barnesin Derivatives

Here, we applied and optimized a solid support (SP)-based Horner-Wadsworth-Emmons reagent to prepare SP-bound vinylogous amino acids. Subsequent SP-based peptide synthesis, global deprotection, and chemical modifications yielded 14 lipodipeptides carrying

Investigating a Boronate-Affinity-Guided Acylation Reaction for Labelling Native Antibodies

The excellent molecular recognition capabilities of monoclonal antibodies (mAbs) have opened up exciting opportunities for biotherapeutic discovery. Taking advantage of the full potential of this tool necessitates affinity ligands capable of conjugating directly with small molecules to a defined degree of biorthogonality, especially when modifying natural Abs. Herein, a bioorthogonal boronate-affinity-based Ab ligand featuring a 4-(dimethylamino)pyridine and an S-aryl thioester to label full-length Abs is reported. The photoactivatable linker in the acyl donor facilitated purification of azide-labelled Ab (N3-Ab) was quantitatively cleaved upon brief exposure to UV light while retaining the original Ab activity. Click reactions enabled the precise addition of biotin, a fluorophore, and a pharmacological agent to the purified N3-Abs. The resulting immunoconjugate showed selectivity against targeted cells. Bioorthogonal traceless design and reagentless purification allow this strategy to be a powerful tool to engineer native antibodies amenable to therapeutic intervention.

Backbone thioamide directed macrocyclisation: Lactam stapling of peptides

A novel method for lactam stapling of Asp/Lys-containing peptides has been developed that does not require coupling agents. A backbone thioamide is incorporated at the N-terminal side of the aspartate residue. Ag(i)-promoted activation of the thioamide in the vicinity of the Asp carboxylate generates a cyclic isoimide intermediate that is trapped by the Lys amine to generate the macrolactam. This method is suitable for generation of i,i+2, i,i+3, and i,i+4-spaced lactam-bridged peptides. This journal is

Synthesis of C-Glycosyl Amino Acid Building Blocks Suitable for the Solid-Phase Synthesis of Multivalent Glycopeptide Mimics

Five C-glycosyl functionalized lysine building blocks, featuring C-glycosidic derivatives of α-rhamnose, α-mannose, α-galactose, β-galactose, and β-N-acetyl glucosamine have been designed and synthesized. These derivatives, equipped with acid-labile protecting groups, are eminently suitable for solid-phase synthesis of multivalent glycopeptides. The lysine building blocks were prepared from C-allyl glycosides that underwent a Grubbs cross-metathesis with an acrylate, followed by a reduction of the C=C double bond in the resulting α,β-unsaturated esters, and liberation of the carboxylate to allow condensation with a lysine side chain. The thus obtained C-glycosides, five in total, were applied in the solid-phase peptide synthesis (SPPS) of three glycopeptides, showing the potential of the described building blocks in the assembly of well-defined mimics of homo- and heteromultivalent glycopeptides and glycoclusters.

NEW TARGETED CYTOTOXIC RATJADONE DERIVATIVES AND CONJUGATES THEREOF

The present invention is directed to novel natural product-derived ratjadone-based compounds useful as payloads (or toxins) in drug-conjugates constructs with cell target binding moieties (CTBM) and payload-linker compounds useful in connection with drug conjugates. The present invention further relates to new ratjadone compositions including the aforementioned payloads, payload-linkers and drug conjugates, and methods for using these payloads, payload-linkers and drug conjugates, to treat pathological conditions including cancer, inflammatory and infectious diseases.

SITE SELECTIVE CONJUGATION OF AN OLIGONUCLEOTIDE CONJUGATE OR A SMALL MOLECULE TO A METAL BINDING PROTEIN

The present invention relates to methods for site selective conjugation of an oligonucleotide conjugate to a metal binding protein comprising a metal binding site and for site selective conjugation of a small molecule conjugation compound (SMCoC) to an antibody comprising a metal binding site, metal binding protein conjugates obtainable by said methods, and uses of said metal binding protein conjugates.

Synthesis and antibacterial activities of amphiphilic neomycin B-based bilipid conjugates and fluorinated neomycin B-based lipids

Investigating the effect of lipid hydrophobicity on the activity of amphiphilic neomycin B conjugates, six polycationic amphiphiles (PAs) were created. Four of the new compounds incorporated either palmitic or arachidic di-lipid lysine tails, while two had single fluorinated undecanoic acid tails. The basicity of half of the compounds was increased through the incorporation of six guanidine moieties, in order to assess the effect of base strength on antimicrobial activity. A panel of ten bacteria was used for the testing, with seven strains obtained from the American Type Culture Collection series and three clinical isolates from Canadian Intensive Care Units. When compared to previous results with hydrocarbon monolipids the PAs all compounds were found to have reduced activity, though the hemolytic activity of the compounds with fluorinated tails was sharply reduced, with only a moderate reduction in antimicrobial activity.

MODULATORS OF PHARMACOKINETIC PROPERTIES OF THERAPEUTICS

The present application provides for a compound of Formula I, or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.

Orthogonality and compatibility between Tsc and Fmoc amino-protecting groups

New deprotection conditions that provide a complete orthogonality between Tsc and Fmoc amino-protecting groups are described. The potential of these orthogonal deprotection conditions was then demonstrated by the efficient solid-phase synthesis of branched peptides 20 and 21 using doubly protected amino acids such as Tsc-Lys(Fmoc)-OH 4c and Fmoc-Lys(Tsc)-OH 4d.

One-pot conversion of benzyl carbamates into fluorenylmethyl carbamates

A simple one-pot procedure smoothly converted N-benzyloxycarbonyl groups into N-fluorenylmethoxycarbonyl groups via hydrogenation with a poisoned catalyst in the presence of Fmoc-OSu. Functional groups such as t-butyl esters, t-butyl ethers, and N-Boc were stable under the reaction conditions. (C) 2000 Elsevier Science Ltd.