847354-75-0Relevant academic research and scientific papers
Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides
Reddy, Kishorkumar M.,Mugesh, Govindasamy
, p. 34 - 43 (2019/01/16)
Selenocysteine (Sec), the 21st proteinogenic amino acid, is inserted co-translationally into number of natural proteins. It is coded by a dual function stop codon UGA (opal). It is a redox active amino acid found at the active sites of several
Preparation of the β2-homoselenocysteine derivatives Fmoc-(S)-β2hSec(PMB)-OH and Boc-(S)-β2hSec(PMB)- OH for solution and solid-phase peptide synthesis
Patora-Komisarska, Krystyna,Jadwiga Podwysocka, Dominika,Seebach, Dieter
experimental part, p. 1 - 17 (2011/03/17)
Fmoc-β2hSer(tBu)-OH was converted to Fmoc-β2hSec(PMB)-OH in five steps. To avoid elimination of HSeR, the selenyl group was introduced in the second last step (Fmoc- β2hSer(Ts)-OAll→Fmoc-β2hSec(PMB)-OAll). In a similar way, the N-Boc-protected compound was prepared. With the β2hSe-derivatives, 21 β2-amino-acid building blocks with proteinogenic side chains are now available for peptide synthesis. Copyright
Synthesis, characterization and antioxidant activity of angiotensin converting enzyme inhibitors
Bhuyan, Bhaskar J.,Mugesh, Govindasamy
experimental part, p. 1356 - 1365 (2011/04/23)
Angiotensin converting enzyme (ACE) catalyzes the conversion of angiotensin I (Ang I) to angiotensin II (Ang II). ACE also cleaves the terminal dipeptide of vasodilating hormone bradykinin (a nonapeptide) to inactivate this hormone. Therefore, inhibition of ACE is generally used as one of the methods for the treatment of hypertension. 'Oxidative stress' is another disease state caused by an imbalance in the production of oxidants and antioxidants. A number of studies suggest that hypertension and oxidative stress are interdependent. Therefore, ACE inhibitors having antioxidant property are considered beneficial for the treatment of hypertension. As selenium compounds are known to exhibit better antioxidant behavior than their sulfur analogues, we have synthesized a number of selenium analogues of captopril, an ACE inhibitor used as an antihypertensive drug. The selenium analogues of captopril not only inhibit ACE activity but also effectively scavenge peroxynitrite, a strong oxidant found in vivo. The Royal Society of Chemistry 2011.
Synthesis of a selenocysteine-containing peptide by native chemical ligation
Gieselman, Matt D.,Xie, Lili,Van Der Donk, Wilfred A.
, p. 1331 - 1334 (2007/10/03)
(equation presented) A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
