28924-92-7Relevant articles and documents
Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct
Rajput, Sunnia,McLean, Kirsty J.,Poddar, Harshwardhan,Selvam, Irwin R.,Nagalingam, Gayathri,Triccas, James A.,Levy, Colin W.,Munro, Andrew W.,Hutton, Craig A.
supporting information, p. 9792 - 9805 (2019/11/13)
A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(l-tyrosyl-l-tyrosine) results in sub-μM binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme FeIII. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.
New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling
Coman, Anca G.,Paraschivescu, Codruta C.,Hadade, Niculina D.,Juncu, Andrei,Vlaicu, Ovidiu,Popescu, Costin-Ioan,Matache, Mihaela
, p. 3917 - 3923 (2016/11/11)
Peptidyl-acyloxymethyl ketones (AOMKs) belong to a class of selective, irreversible inhibitors (activity-based probes) widely used as chemical tools of investigating proteins, for example, in activity-based protein profiling. The synthesis of the AOMKs has always been challenging and current methodologies involve both solution and solid-phase synthesis. Herein, the synthesis of a new scaffold useful for the preparation of peptidyl-AOMKs is reported and it is demonstrated that the new synthetic probes bearing a 4-functionalized 2,6-dimethylbenzoate efficiently inhibit cysteine proteases like cathepsin B.
Unnatural chiral N - Tert -butanesulfinyl α-amino acid synthesis; A general synthetic strategy to N -boc-phenylalanine analogue alternatives
Lin, Li,Fu, Xu,Ma, Xiaojuan,Zhang, Jinlong,Wang, Rui
supporting information, p. 2559 - 2563 (2013/01/13)
This work provides a general approach to unnatural chiral N-tert-butanesulfinyl α-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98:2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2,6-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps. Georg Thieme Verlag Stuttgart · New York.