34078-85-8

Usage

Chemical Properties

White powder

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 2650-64-8 Cbz-L-Gln 

Downstream Products

• 156032-10-9 Z-Gln-Lol 
• 127413-74-5 (2S,3aS,7aS)-1-[(R)-4-((S)-2-Benzyloxycarbonylamino-4-carbamoyl-butyrylamino)-4-carboxy-butyryl]-octahydro-indole-2-carboxylic acid 
• 96235-69-7 Z-Gln-Pheol 

Relevant academic research and scientific papers

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

Direct PCR amplification of various modified DNAs having amino acids: Convenient preparation of DNA libraries with high-potential activities for in vitro selection

We synthesized modified 2′-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucyl, prolyl, glutaminyl, seryl, O-benzyl seryl or threonyl group) gave the corresponding full-length PCR products in good yield. Although dUTP analogues bearing aspartyl, glutamyl or cysteinyl were found to be poor substrates for PCR catalyzed by KOD Dash DNA polymerase, optimization of the reaction conditions resulted in substantial generation of full-length product. In the case of reaction using dUTP analogue having a cysteinyl group, addition of a reducing agent improved the reaction yield. Thus, PCRs using KOD Dash DNA polymerase together with amino acyl dUTP provide convenient and efficient preparation of various modified DNA libraries with potential protein-like activities.

Structure-Activity Study of 5-Substituted 1-Carbobenzoxy-2-iminohydantoins as Potential Anticonvulsant Agents

On the basis of our previous findings, a series of 5-substituted 2-iminohydantoins has been synthesized and tested for anticonvulsant activity to better understand the SAR of 2-iminohydantoins.Among the compounds tested, (S)-(+)-1-carbobenzoxy-2-iminohydantoin analogs with ethyl (6)-, n-propyl (7a)-, isopropyl (8)-, allyl (9)-, and sec-butyl (11)-substituted groups at the C5 of the iminohydanotin ring provided the best activities against the MES test with ED50 values in the range of 52-74 mg/kg.All of the above compounds except 8 also showed activity against the scMET test with ED50 values in the range of 141-223 mg/kg.All significantly active compounds (1, 6, 7a, 8, 9, and 11) possesed aliphatic hydrocarbon side chains of two- to three-carbon lengths at the C5 position.All of the compounds with no or minimal activity had either shorter or longer side chains.The compounds substituted at the C5 position by aryl groups, arylalkyl groups, or alkyl and arylalkyl groups containing heteroatoms also showed no activity against the MES and scMET tests.The results suggested that the C5 side chain with the correct stereochemistry in 2-iminohydantoins provides optimal anticonvulsant activity when the side chains are aliphatic hydrocarbons with a lenght, ignoring branchingg, of two to three carbons.

Dichlorotris(dimethylamino)phosphorane as Dehydration Reagent for the Preparation of Activated (-ONp, -OPcp, -NSu)Esters of N-Protected Multifunctional Amino Acids

Dichlorotris(dimethylamino)phosphorane (5) is an excellent reagent for the preparation of the activated esters of N-protected amino acids 7-9.Besides 4-nitrophenyl-, pentachlorophenyl-, and N-hydroxysuccinimide esters of various N-protected amino acids, in the presence of HOBt benzyloxycarbonyl-threonine N-hydroxysuccinimide ester was obtained for the first time.