6929-40-4

Usage

Purification Methods

Dissolve the acid in NaHCO3 solution, cool and precipitate it by adding N HCl. Collect the solid, dry it at 100o and recrystallise it from MeOH. Note that it is hydrolysed by aqueous 3M, 1M and 0.2M HCl at 120o

InChI:InChI=1/C17H21N3O4S/c21-14(18-11-7-5-10(6-8-11)16(22)23)4-2-1-3-13-15-12(9-25-13)19-17(24)20-15/h5-8,12-13,15H,1-4,9H2,(H,18,21)(H,22,23)(H2,19,20,24)/t12-,13-,15-/m0/s1

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 58-85-5 biotin 
• 35013-72-0 biotin N-Hydroxysuccinimide ester 
• 91853-90-6 biotin chloride 

Downstream Products

• 952705-45-2 4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester 

Relevant academic research and scientific papers

Synthesis and in?vitro anticancer activities of biotinylated derivatives of glaucocalyxin A and oridonin

Fourteen glaucocalyxin A biotinylated derivatives, one glaucocalyxin C biotinylated derivative, and two oridonin biotinylated derivatives were designed and synthesized. Their structures were confirmed from 1H NMR, 13C NMR and HRMS data. The derivatives were evaluated for cytotoxic activities against lung (A549), cervical cancer cell line HeLa derivative (KB), multidrug-resistant KB subline (KB-VIN), triple-negative breast (MDA-MB-231), and estrogen receptor-positive breast (MCF-7) cancer cell lines. (Figure presented.).

Design and synthesis of ATP-based nucleotide analogues and profiling of nucleotide-binding proteins

Two nucleotide-based probes were designed and synthesized in order to enrich samples for specific classes of proteins by affinity-based protein profiling. We focused on the profiling of adenine nucleotide-binding proteins. Two properties were considered in the design of the probes: the bait needs to bind adenine nucleotide-binding proteins with high affinity and carry a second functional group suitable and easily accessible for coupling to a chromatography resin. For this purpose, we synthesized p-biotinyl amidobenzoic acid-ATP (p-BABA-ATP) and p-biotinyl aminomethylbenzoic acid-ATP (p-BAMBA-ATP). p-BABA-ATP and p-BAMBA-ATP both bind to ATP-binding cassette (ABC) proteins with at least 10-fold higher affinity than ATP. Several ABC transporters could be enriched using p-BABA-ATP or p-BAMBA-ATP.

Synthesis of chemiluminescent biotinyl naphtho[1,8-de][1,2]diazepine-1,4- diones

A new chemiluminescent seven numbered cyclic peri hydrazide, 6-amino-2,3-dihydronaphtho[1,8-de][1,2]diazepine-1,4-dione (AH, 4), and five of its biotin conjugates with various spacer groups are synthesized. The total framework of the chemiluminescent biot

Artificial metalloenzymes: (Strept)avidin as host for enantioselective hydrogenation by achiral biotinylated rhodium-diphosphine complexes

We report on the generation of artificial metalloenzymes based on the noncovalent incorporation of biotinylated rhodium-diphosphine complexes in (strept)avidin as host proteins. A chemogenetic optimization procedure allows one to optimize the enantioselectivity for the reduction of acetamidoacrylic acid (up to 96% ee (R) in streptavidin S112G and up to 80% ee (S) in WT avidin). The association constant between a prototypical cationic biotinylated rhodium-diphosphine catalyst precursor and the host proteins was determined at neutral pH: log Ka = 7.7 for avidin (pl = 10.4) and log Ka = 7.1 for streptavidin (pl = 6.4). It is shown that the optimal operating conditions for the enantioselective reduction are 5 bar at 30 °C with a 1% catalyst loading.