113850-76-3Relevant articles and documents
Electron-deficient p-benzoyl-l-phenylalanine derivatives increase covalent chemical capture yields for protein–protein interactions
Joiner, Cassandra M.,Breen, Meghan E.,Mapp, Anna K.
, p. 1163 - 1170 (2019)
The photoactivatable amino acid p-benzoyl-l-phenylalanine (pBpa) has been used for the covalent capture of protein–protein interactions (PPIs) in vitro and in living cells. However, this technique often suffers from poor photocrosslinking yields due to th
Facile synthesis of a novel genetically encodable fluorescent α-amino acid emitting greenish blue light
Gupta, Aakash,Garreffi, Brian P.,Guo, Maolin
, p. 12578 - 12581 (2020)
We report the facile synthesis and characterization of a novel fluorescent α-amino acid 4-phenanthracen-9-yl-l-phenylalanine (Phen-AA) (5) that emits greenish blue light in the visible region. This genetically encodable l-α-amino acid has excellent photostability with a 75% quantum yield. It readily gets into human cells, being clearly imaged upon 405 nm laser excitation. The synthetic procedure is resistant to racemization and only involves three simple steps which use mild conditions and generate the Phen-AA in reasonably good yield. It may find broad applications in research, biotechnology, and the pharmaceutical industry.
A Bifunctional Amino Acid Enables Both Covalent Chemical Capture and Isolation of in Vivo Protein–Protein Interactions
Joiner, Cassandra M.,Breen, Meghan E.,Clayton, James,Mapp, Anna K.
, p. 181 - 184 (2017)
In vivo covalent chemical capture by using photoactivatable unnatural amino acids (UAAs) is a powerful tool for the identification of transient protein–protein interactions (PPIs) in their native environment. However, the isolation and characterization of
Solid-phase, Pd-catalyzed silicon-aryl carbon bond formation. Synthesis of sansalvamide A peptide.
Gu, Wenxin,Liu S, Shouxin,Silverman, Richard B
, p. 4171 - 4174 (2002)
A palladium-catalyzed silicon-aryl carbon bond formation on solid-phase is reported. A phenylalanine silane resin was prepared directly from protected iodo-substituted phenylalanine with butyl diethylsilane polystyrene in one step. A rapid and high-yield solid-phase synthesis of sansalvamide A peptide was achieved from the phenylalanine silane resin. [reaction: see text]
Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes
Hebel, Marco,Riegger, Andreas,Zegota, Maksymilian M.,Kizilsavas, G?nül,Ga?anin, Jasmina,Pieszka, Michaela,Lückerath, Thorsten,Coelho, Jaime A. S.,Wagner, Manfred,Gois, Pedro M. P.,Ng, David Y. W.,Weil, Tanja
, p. 14026 - 14031 (2019)
The development of a synthetic code that enables a sequence programmable feature like DNA represents a key aspect toward intelligent molecular systems. We developed herein the well-known dynamic covalent interaction between boronic acids (BAs) and catechols (CAs) into synthetic nucleobase analogs. Along a defined peptide backbone, BA or CA residues are arranged to enable sequence recognition to their complementary strand. Dynamic strand displacement and errors were elucidated thermodynamically to show that sequences are able to specifically select their partners. Unlike DNA, the pH dependency of BA/CA binding enables the dehybridization of complementary strands at pH 5.0. In addition, we demonstrate the sequence recognition at the macromolecular level by conjugating the cytochrome c protein to a complementary polyethylene glycol chain in a site-directed fashion.
A facile solution and solid phase synthesis of phosphotyrosine mimetic L-4-[diethylphosphono(difluoromethyl)]-phenylalanine (F2Pmp(EtO)2) derivatives
Qabar, Maher N.,Urban, Jan,Kahn, Michael
, p. 11171 - 11178 (1997)
The F2Pmp derivatives were prepared in 80-90% yield from commercially available protected L-4-iodophenylalanine by esterification with diazomethane followed by a CuCl-mediated coupling to (diethylphosphonyl) difluoromethylcadmium bromide. Moreover, treatment of L-4-iodoPhe-containing peptides under the same coupling conditions provided the F2Pmp-containing peptides in very good yields.
Synthesis and protein incorporation of azido-modified unnatural amino acids
Tookmanian, Elise M.,Fenlon, Edward E.,Brewer, Scott H.
, p. 1274 - 1281 (2015)
Two new azidophenylalanine residues (3 and 4) have been synthesized and, in combination with 4-azido-l-phenylalanine (1) and 4-azidomethyl-l-phenylalanine (2), form a series of unnatural amino acids (UAAs) containing the azide vibrational reporter at varying distances from the aromatic ring of phenylalanine. These UAAs were designed to probe protein hydration with high spatial resolution by utilizing the large extinction coefficient and environmental sensitivity of the azide asymmetric stretch vibration. The sensitivity of the azide reporters was investigated in solvents that mimic distinct local protein environments. Three of the four azido-modified phenylalanine residues were successfully genetically incorporated into a surface site in superfolder green fluorescent protein (sfGFP) utilizing an engineered, orthogonal aminoacyl-tRNA synthetase in response to an amber codon with high efficiency and fidelity. SDS-PAGE and ESI-Q-TOF mass analysis verified the site-specific incorporation of these UAAs. The observed azide asymmetric stretch in the linear IR spectra of these UAAs incorporated into sfGFP indicated that the azide groups were hydrated in the protein.
A palladium and gold catalytic system enables direct access to O- and S-linked non-natural glyco-conjugates
Jeon, Min Ho,Mathew, Bijoy P.,Kuram, Malleswara Rao,Myung, Kyungjae,Hong, Sung You
, p. 11518 - 11524 (2016)
Here we report a straightforward cross-coupling method for the synthesis of non-natural glycoamino acids from alkyne-bearing monosaccharides and p-iodophenylalanine. Pd/Au-catalyzed Sonogashira coupling is tolerant to both O- and S-glycosides without any epimerization. In addition, no racemization of the amino acid was observed allowing direct access to the homogeneous glyco-conjugate in a single step. Notably, this Pd/Au catalytic system presents enhanced catalytic activity than conventional Pd/Cu and Pd-only platforms, and it further enables the convergent synthesis of glycodipeptides.
Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides
Cuesta-Galisteo, Sergio,Sch?rgenhumer, Johannes,Wei, Xiaofeng,Merino, Estíbaliz,Nevado, Cristina
supporting information, p. 1605 - 1609 (2020/12/01)
A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.
Preparation method of sacubitril intermediate
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Paragraph 0043-0044; 0046-0047, (2021/04/17)
The invention relates to the technical field of synthesis of medical intermediates, in particular to a preparation method of a sacubitril intermediate, which comprises the following steps: 1) reacting a raw material compound III with phosphorus trihalide to obtain a compound II; and 2) reacting the compound II with phenylhydrazine in the presence of a catalyst and an additive to obtain a sacubitril intermediate, namely a compound I. According to the invention, cheap phosphorus trihalide is selected to replace expensive and highly toxic trifluoromethanesulfonic anhydride, and cheap phenylhydrazine and a catalyst palladium chloride are adopted. The method has the advantages of simple reaction operation, low cost and high yield, and is easier for industrial production of the compound I.
