141215-69-2Relevant articles and documents
TRICARBONYLCHROMIUM TRYPTOPHAN DERIVATIVES AND THEIR USE IN PEPTIDE SYNTHESIS
Sergheraert, C.,Tartar, A.
, p. 163 - 168 (1982)
Incorporation of a Cr(CO)3 ligand into the indole ring of N-α-t-butoxycarbonyl * tryptophan methyl ester was achieved in 47percent yield.The corresponding para-nitrophenyl ester was used in the solid phase synthesis of a peptidic hormone (LHRH) analogue with the aim of decreasing tryptophan alkylation.No improvement was observed.
A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans
Chuang, Kangway V.,Kieffer, Madeleine E.,Reisman, Sarah E.
, p. 4750 - 4753 (2016)
A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(tBu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (-)-aspergilazine A.
Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids
Abas, Hossay,Mas-Roselló, Josep,Amer, Mostafa Mahmoud,Durand, Derek J.,Groleau, Robin R.,Fey, Natalie,Clayden, Jonathan
, p. 2418 - 2422 (2019)
Both E- and Z-N′-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K+ and [18]crown-6 induces intramolecular migration of the alkeny
Enantioselective fluorescent sensors for chiral carboxylates based on calix[4]arenes bearing an L-tryptophan unit
Qing, Guang-Yan,He, Yong-Bing,Wang, Feng,Qin, Hai-Juan,Hu, Chen-Guang,Yang, Xi
, p. 1768 - 1778 (2007)
Two-armed chiral calix[4]arenes (3a-c) functionalized at the lower ring with L-tryptophan units have been prepared and the structures of these receptors characterized by IR, MS, 1H, and 13C NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral recognition abilities towards some enantiomers of chiral materials and formed 1:1 complexes between host and guest. Receptor 3a exhibits excellent enantioselective fluorescent recognition ability towards the N-Boc-protected alanine anion and 3b reveals good enantioselective recognition ability towards the enantiomers of mandelate. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Total synthesis and structural revision of (-)-protubonine A and (-)-protubonine B
Lorenzo, Paula,Alvarez, Rosana,De Lera, Angel R.
, p. 2557 - 2564 (2014)
The proposed structures of (-)-protubonine A and (-)-protubonine B, which are pyrrolidinoindoline diketopiperazine alkaloids that were isolated from the marine-derived fungus Aspergillus sp. SF-5044, have been synthesized and correspond to diastereomers of the natural isolates. The total syntheses, herein, established the stereostructures of the alkaloids as the C-11 epimers of the purported structures. The natural products (-)-protubonine A and (-)-protubonine B have the absolute configuration of (2R,3R,11S,15S), and this has been confirmed by total synthesis. Copyright
Efficient chromatographic resolution of a configurationally fragile atropisomeric diphenol via its N-(α)-Boc-tryptophan diesters
Nechab, Malek,Panchal, Bhavesh M.,Philouze, Christian,Einhorn, Cathy,Einhorn, Jacques
, p. 1681 - 1684 (2005)
Racemic 4,5-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione 2, an atropisomeric diphenol prone to thermal isomerisation, has been efficiently resolved by conversion into its N-(α)-Boc-tryptophan diesters. Easy chromatographic separation of the diastereomeric pair of diesters, followed by ester cleavage under mild conditions gave each enantiomer in good yield and high enantiomeric purity. X-ray diffraction on a single crystal of one of the diastereomeric diesters allowed attribution of the absolute configuration of the stereogenic axes.
Synthesis of ring-A-substituted tryptophan by a palladium-catalyzed heteroannulation reaction
Jia, Yanxing,Zhu, Jieping
, p. 2469 - 2472 (2005)
Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert- butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields. Georg Thieme Verlag Stuttgart.
Enantioselective fluorescent sensors for amino acid derivatives based on BINOL bearing S-tryptophan Unit: Synthesis and chiral recognition
Xu, Kuo-Xi,Cheng, Peng-Fei,Zhao, Jin,Wang, Chao-Jie
, p. 991 - 1000 (2011)
Four novel derivatives of BINOL bearing Stryptophan unit have been prepared and the structures of these compounds characterized by IR, MS, 1H and 13C NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral recognition abilities towards N-Boc-protected amino acid anions and formed 1:1 complexes between host and guest. Receptors exhibit excellent enantioselective fluorescent recognition ability towards the amino acid derivatives. Springer Science+Business Media, LLC 2011.
Catalytic enantioselective transamination of alpha-keto esters: an organic approach to enzymatic reactions.
Knudsen, Kristian Rahbek,Bachmann, Stephan,Jorgensen, Karl Anker
, p. 2602 - 2603 (2003)
The half-transamination reaction of alpha-keto esters with pyridoxamine or 4-picolylamine was found to be catalysed by different metal catalysts in organic solvents giving moderate yields and enantioselectivities of up to 37% ee for methyl-3-indole pyruvate.
Pharmacodynamic and pharmacokinetic profiles of a neurotensin receptor type 2 (NTS2) analgesic macrocyclic analog
Chartier, Magali,Desgagné, Michael,Sousbie, Marc,Rumsby, Charles,Chevillard, Lucie,Théroux, Léa,Haroune, Lounès,C?té, Jér?me,Longpré, Jean-Michel,Boudreault, Pierre-Luc,Marsault, éric,Sarret, Philippe
, (2021)
The current opioid crisis highlights the urgent need to develop safe and effective pain medications. Thus, neurotensin (NT) compounds represent a promising approach, as the antinociceptive effects of NT are mediated by activation of the two G protein-coupled receptor subtypes (i.e., NTS1 and NTS2) and produce potent opioid-independent analgesia. Here, we describe the synthesis and pharmacodynamic and pharmacokinetic properties of the first constrained NTS2 macrocyclic NT(8–13) analog. The Tyr11 residue of NT(8–13) was replaced with a Trp residue to achieve NTS2 selectivity, and a rationally designed side-chain to side-chain macrocyclization reaction was applied between Lys8 and Trp11 to constrain the peptide in an active binding conformation and limit its recognition by proteolytic enzymes. The resulting macrocyclic peptide, CR-01-64, exhibited high-affinity for NTS2 (Ki 7.0 nM), with a more than 125-fold selectivity over NTS1, as well as an improved plasma stability profile (t1/2 > 24 h) compared with NT (t1/2 ~ 2 min). Following intrathecal administration, CR-01-64 exerted dose-dependent and long-lasting analgesic effects in acute (ED50 = 4.6 μg/kg) and tonic (ED50 = 7.1 μg/kg) pain models as well as strong mechanical anti-allodynic effects in the CFA-induced chronic inflammatory pain model. Of particular importance, this constrained NTS2 analog exerted potent nonopioid antinociceptive effects and potentiated opioid-induced analgesia when combined with morphine. At high doses, CR-01-64 did not cause hypothermia or ileum relaxation, although it did induce mild and short-term hypotension, all of which are physiological effects associated with NTS1 activation. Overall, these results demonstrate the strong therapeutic potential of NTS2-selective analogs for the management of pain.
