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.
Preparation of Constrained Unnatural Aromatic Amino Acids via Unsaturated Diketopiperazine Intermediate
Mollica, Adriano,Costante, Roberto,Mirzaie, Sako,Carradori, Simone,Macedonio, Giorgia,Stefanucci, Azzurra,Novellino, Ettore
, p. 2106 - 2110 (2016/11/23)
Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′-dimethyl-tyrosine and 2′,6′-dimehylphenyl-alanine derivatives as handling building blocks for peptide synthesis via unsaturated diketopiperazine (DKP) intermediate.
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.
