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.
Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines
Speckmeier, Elisabeth,Klimkait, Michael,Zeitler, Kirsten
, p. 3738 - 3745 (2018/04/14)
Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.
