2017
DOI: 10.1016/j.chempr.2017.04.003
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Abstract: Here, we describe the development of a highly efficient one-pot ligationdeselenization technology at aspartate and glutamate that enables the synthesis of polypeptides and proteins on unprecedented timescales. The power of the methodology is showcased through the rapid assembly of three thrombininhibiting tick-derived proteins as well as the synthesis of the 21 kDa homodimeric selenoprotein K. This work lays the foundation for the facile synthesis of a range of bioactive polypeptides and proteins in the future… Show more

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Cited by 66 publications
(68 citation statements)
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“…[81] Similarly,( b-Se)-Asp and (g-Se)-Glu were incorporated in the synthesis of selenoprotein Ka nd three thrombin-inhibiting proteins,i n which one-pot ligation-deselenization gave the native proteins. [82] Sec-mediated NCL has been used in the assembly of diselenide- [83] and selenosulfide-containing analogues of bovine pancreatic trypsin inhibitor (BPTI) [73] and the C-terminal segment of ribonucleotide reductase, [72] among others.I n addition, Sec-mediated expressed-protein ligation (EPL), [84] in which the majority of the protein is recombinantly expressed fused to an intein, converted into at hioester,a nd ligated to ap eptide containing Cys or Sec,l ed to the semisynthesis of Sec-containing variants of RNase A, [74] the natural selenoprotein TR3, [85] and the copper metalloprotein azurin. [86] Azurin is ap articularly good candidate for EPL because its active-site Cys112 is located in the C-terminal portion of the protein, and the C112U variant binds copper as well as the original protein does.…”
Section: Selenocysteine In Chemical Protein Synthesis and Semisynthesismentioning
confidence: 99%
“…[81] Similarly,( b-Se)-Asp and (g-Se)-Glu were incorporated in the synthesis of selenoprotein Ka nd three thrombin-inhibiting proteins,i n which one-pot ligation-deselenization gave the native proteins. [82] Sec-mediated NCL has been used in the assembly of diselenide- [83] and selenosulfide-containing analogues of bovine pancreatic trypsin inhibitor (BPTI) [73] and the C-terminal segment of ribonucleotide reductase, [72] among others.I n addition, Sec-mediated expressed-protein ligation (EPL), [84] in which the majority of the protein is recombinantly expressed fused to an intein, converted into at hioester,a nd ligated to ap eptide containing Cys or Sec,l ed to the semisynthesis of Sec-containing variants of RNase A, [74] the natural selenoprotein TR3, [85] and the copper metalloprotein azurin. [86] Azurin is ap articularly good candidate for EPL because its active-site Cys112 is located in the C-terminal portion of the protein, and the C112U variant binds copper as well as the original protein does.…”
Section: Selenocysteine In Chemical Protein Synthesis and Semisynthesismentioning
confidence: 99%
“…[80] Mit einem Prolylselenoesterpeptid als reaktiverem Acyldonor in der Pro-Cys-Ligation, die unter klassischen Bedingungen extrem langsam vonstatten geht, läuft die NCL bedeutend leichter ab. [82] Die Sec-vermittelte NCL wurde unter anderem eingesetzt, um Diselenid- [83] und Selensulfid-haltige Analoga des Rinder-Trypsininhibitors (BPTI) [73] sowie des C-terminalen Segments von Ribonucleotidreduktase [72] zu erzeugen. [82] Die Sec-vermittelte NCL wurde unter anderem eingesetzt, um Diselenid- [83] und Selensulfid-haltige Analoga des Rinder-Trypsininhibitors (BPTI) [73] sowie des C-terminalen Segments von Ribonucleotidreduktase [72] zu erzeugen.…”
Section: Selenocystein In Der Chemischen Protein(semi)syntheseunclassified
“…[97] Im Gegensatz dazu ist die Deselenierung von Sec zu Ala chemoselektiv und hat keine Auswirkungen auf ungeschützte Cys-Reste (Abbildung 10 a). [82,[98][99][100] Darüber hinaus ergibt die Methylierung von Homoselenocystein nach NCL, [101] die in [82,[98][99][100] Darüber hinaus ergibt die Methylierung von Homoselenocystein nach NCL, [101] die in …”
Section: Selenocystein In Der Chemischen Protein(semi)syntheseunclassified
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