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.
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
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
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.
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.
Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions
Vallakati, Ravikrishna,Plotnikov, Abel T.,Altman, Ryan A.
, p. 2261 - 2264 (2019/03/04)
Herein, we report a practical synthesis of 2-D-l-tryptophan via sequential Ir-catalyzed C–H borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc and methyl ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D-L-Tryptophan is stable in many buffers used for biological studies.
Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents
Kondaparla, Srinivasarao,Debnath, Utsab,Dola, Vasantha Rao,Sinha, Manish,Katti, Seturam B.,Soni, Awakash,Srivastava, Kumkum,Puri, Sunil K.
, (2019/01/05)
In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.
