622-33-3Relevant articles and documents
A Pictet-Spengler ligation for protein chemical modification
Agarwal, Paresh,Van Der Weijden, Joep,Sletten, Ellen M.,Rabuka, David,Bertozzi, Carolyn R.
, p. 46 - 51 (2013)
Aldehyde- and ketone-functionalized proteins are appealing substrates for the development of chemically modified biotherapeutics and protein-based materials. Their reactive carbonyl groups are typically conjugated with α-effect nucleophiles, such as substituted hydrazines and alkoxyamines, to generate hydrazones and oximes, respectively. However, the resulting C=N linkages are susceptible to hydrolysis under physiologically relevant conditions, which limits the utility of such conjugates in biological systems. Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet- Spengler reaction of aldehydes and tryptamine nucleophiles. The ligation exploits the bioorthogonal reaction of aldehydes and alkoxyamines to form an intermediate oxyiminium ion; this intermediate undergoes intramolecular C-C bond formation with an indole nucleophile to form an oxacarboline product that is hydrolytically stable. We used the reaction for site-specific chemical modification of glyoxyl- and formylglycine-functionalized proteins, including an aldehyde-tagged variant of the therapeutic monoclonal antibody Herceptin. In conjunction with techniques for site-specific introduction of aldehydes into proteins, the Pictet-Spengler ligation offers a means to generate stable bioconjugates for medical and materials applications.
Oxime ether heterocyclic formamide derivatives and preparation method and application thereof
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Paragraph 0064-0066, (2021/02/13)
The invention provides an oxime ether heterocyclic formamide derivative and a preparation method and application thereof, and particularly relates to the oxime ether heterocyclic formamide derivativeof which the chemical structural general formula is shown in a formula I. The invention discloses the structural general formula, a synthesis method and an application of the oxime ether heterocyclicformamide derivative serving as an insecticide, a bactericide and a plant virus resisting agent. The invention also discloses an application of the insecticidal composition in preventing and treatingagricultural, forestry and horticultural plant insect pests, diseases and virus diseases in combination with agriculturally acceptable auxiliaries or synergists and commercial insecticides, bactericides, plant virus resisting agents and acaricides, and a preparation method of the insecticidal composition in prevention and treatment of agricultural, forestry and horticultural plant insect pests, diseases and virus diseases.
Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
Yu, Chen-Sheng,Wang, Qiao,Bajsa-Hirschel, Joanna,Cantrell, Charles L.,Duke, Stephen O.,Liu, Xing-Hai
, p. 6423 - 6430 (2021/06/28)
Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.
