32331-75-2Relevant academic research and scientific papers
Transition State-Based Sialyltransferase Inhibitors: Mimicking Oxocarbenium Ion by Simple Amide
Guo, Jian,Li, Wenming,Xue, Weiwei,Ye, Xin-Shan
supporting information, p. 2135 - 2141 (2017/03/17)
In the new transition-state based sialyltransferase inhibitors, an amide group was placed at the corresponding C-2 position of CMP-sialic acid to mimic the geometry and charge distribution in the transition state, and simple aromatic or aliphatic rings were used instead of the sialic acid moiety. All synthetic compounds exhibited excellent α(2-6)-sialyltransferase inhibition, resulting in up to a 2600-fold higher affinity for the enzyme than CMP-Neu5Ac, suggesting that amide is a key element for simulating transition-state features.
Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis
Evans, David A.,Kvaerno, Lisbet,Dunn, Travis B.,Beauchemin, Andre,Raymer, Brian,Mulder, Jason A.,Olhava, Edward J.,Juhl, Martin,Kagechika, Katsuji,Favor, David A.
supporting information; experimental part, p. 16295 - 16309 (2009/05/08)
The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the nonacyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.
Rational design of inhibitors of VirA-VirG two-component signal transduction
Maresh, Justin,Zhang, Jin,Tzeng, Yih-Ling,Goodman, Nora A.,Lynn, David G.
, p. 3281 - 3286 (2008/02/08)
VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium.
Asymmetric, anti-selective scandium-catalyzed Sakurai additions to glyoxyamide. Applications to the syntheses of N-Boc D-alloisoleucine and D-isoleucine
Evans, David A.,Aye, Yimon,Wu, Jimmy
, p. 2071 - 2073 (2007/10/03)
An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-Boc D-alloisoleucine and D-isoleucine are described.
Enantioselective syn-selective scandium-catalyzed ene reactions
Evans, David A.,Wu, Jimmy
, p. 8006 - 8007 (2007/10/03)
An enantio- and diastereoselective carbonyl-ene reaction catalyzed by chiral scandium pyridyl bis(oxazoline) (pybox) complexes has been developed. Uniformly high enantiomeric excesses and good yields were observed. Use of trisubstituted olefins generated
