85134-27-6

Upstream product

• 501-53-1 benzyl chloroformate 
• 30040-93-8 (6R,11R)-methyl 11-((tert-butoxycarbonyl)amino)-6-((2-methoxy-2-oxoethyl)carbamoyl)-2,2-dimethyl-4,12-dioxo-3-oxa-8,9-dithia-5,13-diazapentadecan-15-oate 
• 24948-53-6 N-glycine methyl ester disulfide 
• 54784-68-8 N-carbobenzoxy-L-S-(acetamidomethyl)cysteine 
• 78658-27-2 N-carbobenzoxy-L-S-(acetamidomethyl)cysteinylglycine methyl ester 

Downstream Products

• 87532-20-5 2((CH₃)4N)⁽¹⁺⁾*{Fe₄S₄(C₆H₅CH₂OC(O)NHCH(CH₂S)C(O)NHCH₂C(O)OCH₃)4}^(2-)=((CH₃)4N)2{Fe₄S₄(C₁₄H₁₇N₂O₅S)4} 

Relevant academic research and scientific papers

Highly Cytotoxic Bioconjugated Gold(I) Complexes with Cysteine-Containing Dipeptides

Several gold(I) complexes with cysteine-containing dipeptides have been prepared starting from cystine by coupling different amino acids and using several orthogonal protections. The first step is the reaction of cystine, where the sulfur centre is protected as disulfide, with Boc2O in order to protect the amino group, followed by coupling of an amino acid ester; finally the disulfide bridge is broken with mercaptoethanol to afford the dipeptide derivative. Further reaction with [AuCl(PPh3)] gives the gold-dipeptide-phosphine species. Starting from these formally gold(I) thiolate-dipeptide phosphine complexes with the general formula [Au(SR)(PR3)] different structural modifications, such as change in the type of the amino protecting group, the type of phosphine, the number of gold(I) atoms per molecule, or the use of a non-proteinogenic conformationally restricted amino acid ester, were introduced in order to evaluate their influence in the biological activity of the final complexes. The cytotoxic activity, in vitro, of these complexes was evaluated against different tumour human cell lines (A549, MiaPaca2 and Jurkat). The complexes show an outstanding cytotoxic activity with IC50 values in the very low micromolar range. Structure-activity relationship studies from the complexes open the possibility of designing more potent and promising gold(I) anticancer agents. Striking with gold: Gold(I) complexes with cysteine-containing dipeptides were prepared starting from cystine by coupling different amino acids, and using several orthogonal protections. The complexes show excellent cytotoxic activity with IC50 values in the very low micromolar range. The structural changes in the parent compound led to the synthesis of the most effective compound in the cell lines tested, which is the complex with two AuPPh3+ fragments coordinated to the Boc-Cys-Gly-OMe peptide (see scheme).

Positive Shift of Redox POtential of 2- in Dichloromethane

2 (1) and 2 (2) were prepared from 2 and the corresponding peptides as a model of P. aerogenes Fd.A positive shift in redox potential (120 mV) of 2 was observed in dichlor