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2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Tadashi Honda, Eric M. Padegimas, Emilie David, Chitra Sundararajan, Karen T. Liby, Charlotte Williams, Michael B. Sporn, Melean Visnick

Bioorg Med Chem Lett. Author manuscript; available in PMC 2011 Apr 1.

Published in final edited form as: Bioorg Med Chem Lett. 2010 Apr 1; 20(7): 2275–2278. Published online 2010 Feb 6. doi: 10.1016/j.bmcl.2010.02.007

PMCID:: PMC2862379

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A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst

Satoru Matsukawa, Yasutaka Mouri

Molecules. 2015 Oct; 20(10): 18482–18495. Published online 2015 Oct 9. doi: 10.3390/molecules201018482

PMCID:: PMC6332191

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Production of Cyclic Anhydride-Modified Starches

Ryan C. Amos, Julien Mesnager, Michael Kuska, Mario Gauthier

Polymers (Basel) 2021 May; 13(9): 1504. Published online 2021 May 7. doi: 10.3390/polym13091504

PMCID:: PMC8125099

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Data for the synthesis of oligo-γ-glutamylglutamines as model compounds for γ-glutamyltransferases (GGTs) and for normalization of activities of different GGTs

Cinzia Calvio, Fabio Romagnuolo, Francesca Vulcano, Giovanna Speranza, Carlo F. Morelli

Data Brief. 2018 Dec; 21: 576–581. Published online 2018 Oct 6. doi: 10.1016/j.dib.2018.09.116

PMCID:: PMC6202685

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Effect of the Botanical Origin on Properties of RS3/4 Type Resistant Starch

Tomasz Zięba, Małgorzata Kapelko-Żeberska, Artur Gryszkin, Aleksandra Wilczak, Bartosz Raszewski, Radosław Spychaj

Polymers (Basel) 2019 Jan; 11(1): 81. Published online 2019 Jan 7. doi: 10.3390/polym11010081

PMCID:: PMC6402012

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Effects of Acid-Anhydride-Modified Cellulose Nanofiber on Poly(Lactic Acid) Composite Films

Naharullah Jamaluddin, Yu-I Hsu, Taka-Aki Asoh, Hiroshi Uyama

Nanomaterials (Basel) 2021 Mar; 11(3): 753. Published online 2021 Mar 17. doi: 10.3390/nano11030753

PMCID:: PMC8002836

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Snapshot of a phosphorylated substrate intermediate by kinetic crystallography

Helena Käck, Katharine J. Gibson, Ylva Lindqvist, Gunter Schneider

Proc Natl Acad Sci U S A. 1998 May 12; 95(10): 5495–5500. doi: 10.1073/pnas.95.10.5495

PMCID:: PMC20405

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Stereoelectronic Features of a Complex Ketene Dimerization Reaction

Robert D. Barrows, Mark J. Dresel, Thomas J. Emge, Paul R. Rablen, Spencer Knapp

Molecules. 2022 Jan; 27(1): 66. Published online 2021 Dec 23. doi: 10.3390/molecules27010066

PMCID:: PMC8746406

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A model of the pressure dependence of the enantioselectivity of Candida rugosalipase towards (±)-menthol

Ulrich H.M. Kahlow, Rolf D. Schmid, Jürgen Pleiss

Protein Sci. 2001 Oct; 10(10): 1942–1952. doi: 10.1110/ps.12301

PMCID:: PMC2374222

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Sensitivity of Neurospora crassa to a Marine-Derived Aspergillus tubingensis Anhydride Exhibiting Antifungal Activity That Is Mediated by the MAS1 Protein

Liat Koch, Anat Lodin, Inbal Herold, Micha Ilan, Shmuel Carmeli, Oded Yarden

Mar Drugs. 2014 Sep; 12(9): 4713–4731. Published online 2014 Sep 1. doi: 10.3390/md12094713

PMCID:: PMC4178490

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Development of organophosphate hydrolase activity in a bacterial homolog of human cholinesterase

Patricia M. Legler, Susanne M. Boisvert, Jaimee R. Compton, Charles B. Millard

Front Chem. 2014; 2: 46. Published online 2014 Jul 16. doi: 10.3389/fchem.2014.00046

PMCID:: PMC4100338

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Site-specific quantification of lysine acetylation in the N-terminal tail of histone H4 using a double-labelling, targeted UHPLC MS/MS approach

Annalisa D’Urzo, Alexander P. Boichenko, Thea van den Bosch, Jos Hermans, Frank Dekker, Vincenza Andrisano, Rainer Bischoff

Anal Bioanal Chem. 2016; 408: 3547–3553. Published online 2016 Mar 11. doi: 10.1007/s00216-016-9431-1

PMCID:: PMC4837199

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Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols

Matay Kaplan, Michael Ciesielski, Sabine Fuchs, Christoffer Getterle, Frank Schönberger, Rudolf Pfaendner

Polymers (Basel) 2023 Aug; 15(15): 3195. Published online 2023 Jul 27. doi: 10.3390/polym15153195

PMCID:: PMC10420857

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Effects of Fatty Acid Anhydride on the Structure and Thermal Properties of Cellulose-g-Polyoxyethylene (2) Hexadecyl Ether

Wanyong Yu, Na Han, Yongqiang Qian, Xingxiang Zhang, Wei Li

Polymers (Basel) 2018 May; 10(5): 498. Published online 2018 May 4. doi: 10.3390/polym10050498

PMCID:: PMC6415507

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Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property

Yanju Lu, Zhendong Zhao, Liangwu Bi, Yuxiang Chen, Jing Wang, Shichao Xu

Sci Rep. 2018; 8: 2399. Published online 2018 Feb 5. doi: 10.1038/s41598-018-20695-5

PMCID:: PMC5799196

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Surface modification of cellulose nanocrystals with different acid anhydrides for improved dispersion in poly(butylene succinate)

Yingying He, Jiang Zhu, Wentao Wang, Haitao Ni

RSC Adv. 2018 Nov 14; 8(67): 38305–38314. Published online 2018 Nov 14. doi: 10.1039/c8ra07597b

PMCID:: PMC9089815

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Study on Chain Extension Blending Modification and Foaming Behavior of Thermoplastic Polyamide Elastomer

Yuyin Zhao, Jiaxin Zheng, Pei Guo, Congxiao Wang, Menghao Guo, Chunling Xin, Yadong He

ACS Omega. 2023 Mar 21; 8(11): 9832–9842. Published online 2023 Mar 6. doi: 10.1021/acsomega.2c06285

PMCID:: PMC10034832

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Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands

Aubrie A. Harland, Aaron M. Bender, Nicholas W. Griggs, Chao Gao, Jessica P. Anand, Irina D. Pogozheva, John R. Traynor, Emily M. Jutkiewicz, Henry I. Mosberg

J Med Chem. 2016 May 26; 59(10): 4985–4998. Published online 2016 May 5. doi: 10.1021/acs.jmedchem.6b00308

PMCID:: PMC4885601

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One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems

Rodion Lebedev, Dmitry Dar’in, Grigory Kantin, Olga Bakulina, Mikhail Krasavin

Molecules. 2022 Dec; 27(23): 8130. Published online 2022 Nov 22. doi: 10.3390/molecules27238130

PMCID:: PMC9735558

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The Castagnoli–Cushman Reaction

José Luis Ramiro, Sonia Martínez-Caballero, Ana G. Neo, Jesús Díaz, Carlos F. Marcos

Molecules. 2023 Mar; 28(6): 2654. Published online 2023 Mar 15. doi: 10.3390/molecules28062654

PMCID:: PMC10058692

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PMC Images search for acid-anhydride

Figure 2

Structures of oleanonic acid anhydride and lupane anhydride 2

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Bioorg Med Chem Lett. ;20(7):2275-2278.
Figure 1

Structures of oleanolic acid, CDDO, CDDO-Me, betulinic acid and acetoxybetulinic acid anhydride

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Bioorg Med Chem Lett. ;20(7):2275-2278.
Scheme 1

The semi-synthesis transformation of sipholenol A (1) into analogs 8 and 9. Reagents and conditions: (1) acid anhydride, MDAP, anhydrous CH₂Cl₂; (2) p-toluenesulfonic acid, CHCl₃; (3) acid anhydride, MDAP, anhydrous CH₂Cl₂.

Marine Natural Products as Models to Circumvent Multidrug Resistance

Molecules. 2016 Jul;21(7):892.
Scheme 1(I) Formation of a Citric Acid Anhydride Intermediate from Citric Acid and the Subsequent Reaction of the N-Terminal Amine with the Anhydride and (II) Four Possible Products of the Reaction

+174A and +174B represent adducts formed between the N-terminal amine and the citric acid anhydride. The +156A and +156B represent the subsequent imide products (5 and 6-membered rings, respectively) resulting from the cyclization of the newly formed amide and another carboxylic acid in citric acid. There are three carboxylic acids in citric acid: two are equivalent as denoted by the red dots and the other by the blue dot.

Discovery of a Chemical Modification by Citric Acid in a Recombinant Monoclonal Antibody

Anal Chem. 2014 Sep 16;86(18):8932-8936.