51871-42-2Relevant articles and documents
Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides
Zhu, Feng,O'Neill, Sloane,Rodriguez, Jacob,Walczak, Maciej A.
supporting information, p. 7091 - 7095 (2018/05/29)
Reported is the stereospecific cross-coupling of anomeric stannanes with symmetrical diselenides, resulting in the synthesis of selenoglycosides with exclusive anomeric control. The reaction proceeds without the need for directing groups and is compatible
Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues
Hansen, Finn K.,Ha, Khanh,Todadze, Ekaterina,Lillicotch, Aaron,Frey, Alexander,Katritzky, Alan R.
supporting information; experimental part, p. 7162 - 7167 (2011/11/14)
An efficient approach for the synthesis of a series of S-acyl peptides containing internal cysteine residues has been developed and the chemical long-range ligation of these S-acyl peptides via 5-, 8-, 11- and 14-membered cyclic transition states has been
Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis
Voelkert, Martin,Koul, Surrinder,Mueller, Gernot H.,Lehnig, Manfred,Waldmann, Herbert
, p. 6902 - 6910 (2007/10/03)
The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.