68835-84-7Relevant academic research and scientific papers
Naphthoquinones as covalent reversible inhibitors of cysteine proteases—studies on inhibition mechanism and kinetics
Barthels, Fabian,Distler, Ute,Engel, Volker,Engels, Bernd,Hellmich, Ute A.,Johe, Patrick,Klein, Philipp,Le, Thien Anh,Opatz, Till,Schirmeister, Tanja,Schmid, Paul,Tenzer, Stefan,Wagner, Annika
supporting information, (2020/05/16)
The facile synthesis and detailed investigation of a class of highly potent protease inhibitors based on 1,4‐naphthoquinones with a dipeptidic recognition motif (HN‐L‐Phe‐L‐Leu‐OR) in the 2‐position and an electron‐withdrawing group (EWG) in the 3‐positio
Lead Optimization of 2-Phenylindolylglyoxylyldipeptide Murine Double Minute (MDM)2/Translocator Protein (TSPO) Dual Inhibitors for the Treatment of Gliomas
Daniele, Simona,La Pietra, Valeria,Barresi, Elisabetta,Di Maro, Salvatore,Da Pozzo, Eleonora,Robello, Marco,La Motta, Concettina,Cosconati, Sandro,Taliani, Sabrina,Marinelli, Luciana,Novellino, Ettore,Martini, Claudia,Da Settimo, Federico
, p. 4526 - 4538 (2016/06/13)
In glioblastoma multiforme (GBM), translocator protein (TSPO) and murine double minute (MDM)2/p53 complex represent two druggable targets. We recently reported the first dual binder 3 possessing a higher anticancer effect in GBM cells than the standards P
Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine
Zhang, Chi,Liu, Shan-Shan,Sun, Bo,Tian, Jun
supporting information, p. 4106 - 4109 (2015/09/01)
6-(3,5-Bis(trifluoromethyl)phenyl)-1H,4H-2aλ3-ioda-2,3-dioxacyclopenta[hi]indene-1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the pentapeptide leu-enkephalin in protected form. It is worth noting that 1a can be regenerated readily after reaction.
Triazolo-β-aza-ε-amino acid and its aromatic analogue as novel scaffolds for β-turn peptidomimetics
Bag, Subhendu Sekhar,Jana, Subhashis,Yashmeen, Afsana,De, Suranjan
supporting information, p. 5242 - 5245 (2015/03/30)
Triazolo-β-aza-ε-amino acid and its aromatic analogue (AlTAA/ArTAA) in the peptide backbone mark a novel class of conformationally constrained molecular scaffolds to induce β-turn conformations. This was demonstrated forAlTAA in a Leu-enkephalin analogue and in a designed pentapeptide wherein the FRET process was established. Restricted rotation induced chirality and turn conformation into the achiral aromatic amino acid scaffold,ArTAA, which in a short tripeptide backbone acted as a β-turn mimic as a β-sheet folding nucleator. This journal is
Furan-based locked Z -vinylogous γ-amino acid stabilizing protein α-turn in water-soluble cyclic α3γ tetrapeptides
Krishna, Yarkali,Sharma, Shrikant,Ampapathi, Ravi S.,Koley, Dipankar
supporting information, p. 2084 - 2087 (2014/05/06)
Described here is the design, synthesis, and conformational analysis of cyclic tetrapeptides (CTPs) with α3γ architecture containing a furan-based locked Z-vinylogous amino acid (Vaa). This unnatural amino acid locks into a γ-turn that induces
New stable backbone linker resins for solid-phase peptide synthesis.
Gu, Wenxin,Silverman, Richard B
, p. 415 - 418 (2007/10/03)
[reaction: see text] Two new 4-methoxybenzaldehyde backbone linker resins were developed for the solid-phase synthesis of peptides. The linkers are very stable during the cleavage of common protecting groups for amines (Fmoc, Boc) and carboxylic acids (Me, All, tBu) in peptide synthesis. Cleavage from the resin with refluxing TFA is sufficiently mild for peptides containing polar and nonpolar amino acids.
Synthesis and conformational studies of peptidomimetics containing a carbocyclic 1,3-diacid
Chakraborty, Tushar K,Ghosh, Animesh,Nagaraj,Ravi Sankar,Kunwar, Ajit C
, p. 9169 - 9175 (2007/10/03)
A rigid carbocyclic scaffold comprising of an all-cis 4,5-dihydroxy-1,3-cyclopentanedicarboxylic acid is developed. Attachment of peptide strands to the carboxylic groups of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by circular dichroism and NMR studies revealed that these molecules adopt a unique folded structure in nonpolar solvent involving intramolecular hydrogen bonding between PheNH of one strand and LeuC=O (in 2) or GlyC=O (in 3) of the other strand. This structure is very different from the structures observed earlier in their sugar counterparts (1). The paper describes in detail the synthesis and structural studies of compounds 2 and 3.
Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides
Cleij, Marco C.,Scrimin, Paolo,Tecilla, Paolo,Tonellato, Umberto
, p. 5592 - 5599 (2007/10/03)
Several structurally simple N-monoalkylated and -dialkylated dipeptides made of α-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 × 103 and > 104, respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions can form neutral complexes at the pH value of the source phase.
