149834-58-2

Usage

Chemical compound

Used in organic synthesis and as a protecting group for amines in peptide chemistry.

Physical state

Solid

Color

White to light yellow

Soluble in organic solvents

Dimethylformamide, dichloromethane, and tetrahydrofuran
b. Sparingly soluble in water

Melting point

Around 128-132 degrees Celsius

Main use

As a reagent in organic chemistry for protecting amine groups in peptide synthesis and other reactions.

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 76-83-5 trityl chloride 
• 519-73-3 triphenylmethane 

Downstream Products

• 288590-34-1 C₅₈H₅₉N₇O₃S₂ 
• 680190-20-9 2-chloro-6-(6-tritylaminohexyl)aminopurine-2'-deoxy-3',5'-ditoluoyl-β-D-riboside 
• 1092791-63-3 N-(N'-tritylaminohexyl)-α-D-mannopyranosylamine 
• 1207862-70-1 cs124CF₃-CH₂C(O)-NH(CH₂)6NH-Tr 
• 263162-48-7 5-[(3aS,4S,6aR,) -2-oxohexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-(6-aminohexyl)pentanamide hydrochloride 
• 1359968-64-1 C₂₈H₂₉Cl₂N₅ 
• 680190-22-1 2-benzyloxy-6-(6-tritylaminohexyl)aminopurine-3'-acetyl-2'-deoxy-5'-O-p,p'-dimethoxytrityl-β-D-riboside 
• 376631-70-8 2-benzyloxy-6-(6-trifluoroacetamidohexyl)aminopurine-3'-acetyl-5'-triphosphoryl-2'-deoxy-β-D-riboside 
• 680190-21-0 2-benzyloxy-6-(6-tritylaminohexyl)aminopurine-2'-deoxy-β-D-riboside 
• 376631-69-5 2-benzyloxy-6-(6-trifluoroacetamidohexyl)aminopurine-3'-acetyl-2'-deoxy-β-D-riboside 
• 376631-68-4 2-benzyloxy-6-(6-aminohexyl)aminopurine-3'-acetyl-2'-deoxy-β-D-riboside 

Relevant academic research and scientific papers

Synthesis of minoxidil conjugates and their evaluation as HL-60 differentiation agents

Activation of minoxidil (MNX) with N,N′-carbonyldiimidazole and coupling with natural polyamines (PAs) and commercially available aliphatic or aromatic amines provided a series of new conjugates which were evaluated for their ability to induce differentia

Diselenolane-Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein-Coated Quantum Dots

Cyclic oligochalcogenides are emerging as powerful tools to penetrate cells. With disulfide ring tension maximized, selenium chemistry had to be explored next to enhance speed and selectivity of dynamic covalent exchange on the way into the cytosol. We show that diseleno lipoic acid (DiSeL) delivers a variety of relevant substrates. DiSeL-driven uptake of artificial metalloenzymes enables bioorthogonal fluorophore uncaging within cells. Binding of a bicyclic peptide, phalloidin, to actin fibers evinces targeted delivery to the cytosol. Automated tracking of diffusive compared to directed motility and immobility localizes 79 % of protein-coated quantum dots (QDs) in the cytosol, with little endosomal capture (0.06 %). These results suggest that diselenolanes might act as molecular walkers along disulfide tracks in locally denatured membrane proteins, surrounded by adaptive micellar membrane defects. Miniscule and versatile, DiSeL tags are also readily available, stable, soluble, and non-toxic.

SITE-SPECIFIC ANTIBODY-DRUG GLYCOCONJUGATES AND METHODS

Compounds, compositions, and methods are provided for covalently linking an antibody or an antibody fragment to a cargo molecule, such as a therapeutic or a diagnostic agent, using a combination of enzymatic glycan remodeling and click chemistry. The meth

Application of BODIPY-trimethylmelamine conjugate for DNA crosslinking in vitro

The conjugate of the fluorescent dye 4,4,-difluoro-1,3,5,7-tetramethyl-4- bora-3a,4a-diaza-s-indasten-8-propionic acid (BODIPY) with N2,N 4,N6-trimethylmelamine was obtained. This compound was shown to generate covalent crosslinks between DNA strands in vitro in the presence of formaldehyde.

Trityl-derivatized carbohydrates immobilized on a polystyrene microplate

Carbohydrate biosensors, including carbohydrate arrays, are attracting increased attention for the comprehensive and high-throughput investigation of protein-carbohydrate interactions. Here, we describe an effective approach to fabricating a robust microp

Nucleic Acid Analysis Using an Expanded Genetic Alphabet to Quench Fluorescence

Organic chemistry has made possible the synthesis of molecules that expand on Nature's genetic alphabet. Using the previously described nonstandard DNA base pair constructed from isoguanine and 5-methylisocytosine, we report a highly specific and sensitiv

Synthesis and evaluation of oligo-1,3-thiazolecarboxamide derivatives as HIV-1 reverse transcriptase inhibitors

A set of oligo-1,3-thiazolecarboxamide derivatives able to interact with the minor groove of nucleic acids was synthesized. These oligopeptides contained different numbers of thiazole units presenting dimethylaminopropyl or EDTA moieties on the C-terminus, and aminohexanoyl or EDTA moieties on the N-terminus. The inhibition of such compounds on HIV-1 reverse transcriptase activity was evaluated using different model template-primer duplexes: DNA·DNA, RNA·DNA, DNA·RNA and RNA·RNA. The biological properties of the thiazolecarboxamide derivatives were compared to those of distamycin, another minor groove binder which contains three pyrrole rings. Similar to distamycin, the thiazole containing oligopeptides were good inhibitors of the reverse transcription reaction in the presence of DNA·DNA. But in contrast to distamycin, the oligothiazolide derivatives were able to inhibit reverse transcription in the presence of RNA·DNA or DNA·RNA template-primers. Both distamycin and oligothiazolecarboxamides had low affinity for RNA·RNA duplexes. The inhibition obtained with the newly synthesized thiazolecarboxamides showed that these compounds were more powerful and versatile inhibitors of the RT-dependent polymerization than the natural minor groove binder distamycin. (C) 2000 Elsevier Science Ltd.

Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: The oligo-1,3-thiazolecarboxamide derivatives

Human immunodeficiency virus type 1 (HIV-1) integrase (IN) is an essential enzyme in the life cycle of the retrovirus, responsible for catalysing the insertion of the viral genome into the host cell chromosome. For this reason it provides an attractive target for antiviral drug design. We synthesized a series of novel thiazole (Tz)-containing oligopeptides (TCOs; oligo-1,3-thiazolecarboxamides), specifically interacting within the minor groove of DNA. The oligocarboxamide derivatives contained 1-4 Tz rings and different N- and C-terminal groups. The effect of these oligocarboxamides on the HIV-1 IN-catalysed reaction was investigated. Some of the compounds were able to inhibit the reaction. The inhibitory effect of the TCOs increased with the number of Tz units. The structure of various additional positively and/or negatively charged groups attached to the N- and C-termini of TCOs had a pronounced effect on their interaction with the DNA substrate complexed to IN. Modified TCOs having a better affinity for this complex should provide a rationale for the design of drugs targeting the integration step. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

The Synthesis of New Polymer Derivatives of ATP by Radical Copolymerization and Their Coenzymic Activity

Three polymerizable ATP derivatives N6--, N6-ethyl>carbomoylmethyl>- and N6-carbom