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
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
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.
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.
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.
Total Synthesis of Seongsanamide B
Hutton, Craig A.,Shabani, Sadegh
supporting information, (2020/06/05)
The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach employed solid-phase peptide synthesis of a core heptapeptide, incorporating on-resin esterification, followed by solution-phase macrolactamization and a late stage intramolecular Evans-Chan-Lam coupling to generate the biaryl ether of the isodityrosine unit.
