51608-63-0Relevant articles and documents
A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation
Christian, Alec H.,Jia, Shang,Cao, Wendy,Zhang, Patricia,Meza, Arismel Tena,Sigman, Matthew S.,Chang, Christopher J.,Toste, F. Dean
, p. 12657 - 12662 (2019/09/04)
We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C=O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.
Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate
Verardo, Giancarlo,Venneri, Cesare Daniele,Esposito, Gennaro,Strazzolini, Paolo
scheme or table, p. 1376 - 1384 (2011/04/17)
Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.
N-propargylamides via the asymmetric Michael addition of B-alkynyl-10-TMS-9-borabicyclo[3.3.2]decanes to N-acylimines
Gonzalez, Ana Z.,Canales, Eda,Soderquist, John A.
, p. 3331 - 3334 (2007/10/03)
The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemis
A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin
Xu, Zhenrong,Lu, Xiyan
, p. 5031 - 5041 (2007/10/03)
The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.
