64152-76-7Relevant academic research and scientific papers
An effective and safe enkephalin analog for antinociception
Durgarao Viswanadham,B?ttger, Roland,Hohenwarter, Lukas,Nguyen, Anne,Rouhollahi, Elham,Smith, Alexander,Tsai, Yi-Hsuan,Chang, Yuan-Yu,Ortiz, Christopher Llynard,Yang, Lee-Wei,Jimenez, Liliana,Li, Siyuan,Hur, Chan,Li, Shyh-Dar
, (2021/07/10)
Opioids account for 69,000 overdose deaths per annum worldwide and cause serious side effects. Safer analgesics are urgently needed. The endogenous opioid peptide Leu-Enkephalin (Leu-ENK) is ineffective when introduced peripherally due to poor stability a
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
Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls
Coombs, Gavin,Sak, Marcus H.,Miller, Scott J.
, p. 2875 - 2880 (2020/01/24)
We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2-symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3′-disubstituted BINOLs, such as (R)-TRIP, with good (94:6 e.r.) to excellent (>99.9:0.1 e.r.) enantioselectivity after recrystallization, and a diastereoselective net arylation of the minimally modified nonsteroidal anti-inflammatory drug (NSAID) naproxen.
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones
Shugrue, Christopher R.,Featherston, Aaron L.,Lackner, Rachel M.,Lin, Angela,Miller, Scott J.
supporting information, p. 4491 - 4504 (2018/04/26)
Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.
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
Peptide Mechanosynthesis by Direct Coupling of N-Protected α-Amino Acids with Amino Esters
Porte, Vincent,Thioloy, Marion,Pigoux, Titouan,Métro, Thomas-Xavier,Martinez, Jean,Lamaty, Frédéric
supporting information, p. 3505 - 3508 (2016/07/28)
In view of developing alternatives to classical peptide synthesis strategies that suffer from low efficacy and negative environmental impact, the reactivity of N-protected α-amino acids, amino esters, and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide was
Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination
Metrano,Abascal,Mercado,Paulson,Miller
supporting information, p. 4816 - 4819 (2016/04/09)
We describe herein a crystallographic and NMR study of the secondary structural attributes of a β-turn-containing tetra-peptide, Boc-Dmaa-d-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-d-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I′ β-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.
Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties
Laville, Rmi,Nguyen, Thanh Binh,Moriou, Cline,Petek, Sylvain,Debitus, Ccile,Al-Mourabit, Ali
, p. 1351 - 1366 (2015/03/04)
Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.
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
