126705-22-4Relevant articles and documents
Convenient synthesis and isolation of 1-aminocyclopropane-1-carboxylic acid (ACC) and N-protected ACC derivatives
Allwein, Shawn P.,Secord, Elizabeth A.,Martins, Andrew,Mitten, Jeffrey V.,Nelson, Todd D.,Kress, Michael H.,Dolling, Ulf H.
, p. 2489 - 2492 (2004)
A convenient route to 1-aminocyclopropane-1-carboxylic acid (1, ACC) and N-protected derivatives was developed. This route utilizes a bisalkylation of an O-benzyl glycine derived imine followed by global deprotection via hydrogenation. Direct isolation of ACC from a non-aqueous stream or efficient conversion to N-protected derivatives in a single flask is described.
Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins
Nicolaou,Yin, Jun,Mandal, Debashis,Erande, Rohan D.,Klahn, Philipp,Jin, Michael,Aujay, Monette,Sandoval, Joseph,Gavrilyuk, Julia,Vourloumis, Dionisios
supporting information, p. 1698 - 1708 (2016/02/20)
A streamlined total synthesis of N14-desacetoxytubulysin H (Tb1) based on a C-H activation strategy and a short total synthesis of pretubulysin D (PTb-D43) are described. Applications of the developed synthetic strategies and technologies to the synthesis of a series of tubulysin analogues (Tb2-Tb41 and PTb-D42) are also reported. Biological evaluation of the synthesized compounds against an array of cancer cells revealed a number of novel analogues (e.g., Tb14), some with exceptional potencies against certain cell lines [e.g., Tb32 with IC50 = 12 pM against MES SA (uterine sarcoma) cell line and 2 pM against HEK 293T (human embryonic kidney) cell line], and a set of valuable structure-activity relationships. The highly potent cytotoxic compounds discovered in this study are highly desirable as payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies.
Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids
O'Donnell, Martin J.,Alsina, Jordi,Scott, William L.
, p. 8403 - 8406 (2007/10/03)
Alkylation of the benzophenone imine of glycine Wang resin with α,ω-dihaloalkanes yielded valuable reactive intermediates. These racemic ω-chloro or ω-bromo intermediates were converted to α-amino acids containing diverse side-chain functionalities (e.g.
Novel selective inhibitors of the interaction of individual nuclear hormone receptors with a mutually shared steroid receptor coactivator 2
Geistlinger, Timothy R.,Guy, R. Kiplin
, p. 6852 - 6853 (2007/10/03)
Nuclear hormone receptor (NR) signaling, currently a therapeutic target in multiple diseases, involves an ordered series of protein interactions to regulate transcription in response to changing hormone levels. Later steps in the process of ligand-dependent signaling are driven by a highly conserved interaction between the NRs and the steroid receptor coactivators (SRCs) that is effected by a conserved interaction motif (L1XXL2L3), known as an NR box. Using computational design and combinatorial chemistry, we have produced novel ∞-helical proteomimetics of the second NR box of SRC2 that exploit structural differences between human estrogen receptor ∞ (hER∞), human estrogen receptor β (hERβ), and human thyroid hormone receptor β (hTRβ). The resulting library sequentially replaced each leucine with non-natural side chains. Screening this library using a quantitative competition assay revealed compounds that selectively inhibit the interaction of SRC2-2 with each individual NR in preference to its interaction with the other NR. This approach generated highly selective compounds from one that had no specificity for a particular family member. These compounds represent the first family-member-selective competitive inhibitors of the protein interactions of transcription factors. Copyright
