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Article ; Online: An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B.

Hewage, Ranuka T / Huang, Rou-Jie / Lai, Shu-Jung / Lien, Ya-Chu / Weng, Shao-Hsing / Li, Dehai / Chen, Yu-Ju / Wu, Shih-Hsiung / Chein, Rong-Jie / Lin, Hsiao-Ching

Organic letters

2021 Volume 23, Issue 5, Page(s) 1904–1909

Abstract: Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B ( ...

Abstract	Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B (
MeSH term(s)	Diterpenes/chemistry ; Imidazoles/chemistry ; Molecular Structure ; Ovomucin/biosynthesis ; Ovomucin/chemistry
Chemical Substances	Diterpenes ; Imidazoles ; Ovomucin (37281-36-0) ; meleagrin (5780K492K3) ; imidazole (7GBN705NH1)
Language	English
Publishing date	2021-02-11
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.1c00330
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B

Hewage, Ranuka T / Huang, Rou-Jie / Lai, Shu-Jung / Lien, Ya-Chu / Weng, Shao-Hsing / Li, Dehai / Chen, Yu-Ju / Wu, Shih-Hsiung / Chein, Rong-Jie / Lin, Hsiao-Ching

Organic letters. 2021 Feb. 11, v. 23, no. 5

2021

Abstract: ... Con-ABH) was shown to catalyze an aza-Michael addition between 1 and imidazole to give 3S-imidazolyl ...

Abstract	Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (−)-conidiogenone B (1), which involves a diterpene synthase and a P450 monooxygenase. In addition, an α,β-hydrolase (Con-ABH) was shown to catalyze an aza-Michael addition between 1 and imidazole to give 3S-imidazolyl conidiogenone B (6). Compound 6 was more potent than 1 against Staphylococcus aureus strains.
Keywords	Staphylococcus aureus ; biosynthesis ; diterpenoids ; hybrids ; imidazole
Language	English
Dates of publication	2021-0211
Size	p. 1904-1909.
Publishing place	American Chemical Society
Document type	Article
Note	NAL-AP-2-clean
ISSN	1523-7052
DOI	10.1021/acs.orglett.1c00330
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: α(δ')-Michael addition of alkyl amines to dimethyl (E)-hex-2-en-4-ynedioate: synthesis of α,β-dehydroamino acid derivatives.

Chavan, Arjun S / Deng, Jie-Cheng / Chuang, Shih-Ching

Molecules (Basel, Switzerland)

2013 Volume 18, Issue 3, Page(s) 2611–2622

Abstract: The direct nucleophilic addition of alkyl amines to the α(δ')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate α,β-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines ...

Abstract	The direct nucleophilic addition of alkyl amines to the α(δ')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate α,β-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the α-selective nucleophilic conjugate addition to conjugated dimethyl (E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.
MeSH term(s)	Amines/chemical synthesis ; Amines/chemistry ; Amino Acids/chemical synthesis ; Amino Acids/chemistry ; Chemistry, Organic
Chemical Substances	Amines ; Amino Acids
Language	English
Publishing date	2013-02-27
Publishing country	Switzerland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules18032611
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Article ; Online: One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ')-Michael reactions of phosphines with an enyne and N-tosyl aldimines.

Lin, Yu-Wei / Deng, Jie-Cheng / Hsieh, You-Zung / Chuang, Shih-Ching

Organic & biomolecular chemistry

2014 Volume 12, Issue 1, Page(s) 162–170

Abstract: We demonstrate a straightforward synthesis of γ-lactams possessing an α-phosphorus ylide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial α(δ')-attack of phosphines to an enyne in up to 79% yield. The investigated ... ...

Abstract	We demonstrate a straightforward synthesis of γ-lactams possessing an α-phosphorus ylide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial α(δ')-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triarylphosphines and electron-poor aldimines to give γ-lactams in one pot. One of the lactams, with the tri(p-tol)phosphine and 4-cyanophenyl moiety, exhibits fluorescence emission at 447 nm with a quantum yield of 0.11.
Language	English
Publishing date	2014-01-07
Publishing country	England
Document type	Journal Article
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/c3ob41811a
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Article ; Online: A serendipitous C-C bond formation reaction between Michael donors and diiminoquinoid ring assisted by quaternary ammonium fluoride.

Paike, Vijaykumar V / Balakumar, R / Chen, Hsin-Yu / Shih, Hong-Pin / Han, Chien-Chung

Organic letters

2009 Volume 11, Issue 24, Page(s) 5586–5589

Abstract: ... the typical Michael addition fashion and proceeds to completion within 1 h at 70 degrees C in acetonitrile ...

Abstract	An efficient C-C bond formation reaction assisted by a fluoride ion has been identified for N,N'-diphenyl-1,4-phenylenediimine with the compounds having an active methylene group. The reaction follows the typical Michael addition fashion and proceeds to completion within 1 h at 70 degrees C in acetonitrile in the presence of tetrabutylammonium fluoride (TBAF), while the same reaction failed to proceed in the absence of a fluoride anion. The new finding reported herein also offers an unprecedented method for a direct functionalization of polyaniline backbone with versatile functional alkyl groups.
Language	English
Publishing date	2009-12-17
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/ol9025843
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Article ; Online: α(δ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate

Jie-Cheng Deng / Arjun S. Chavan / Shih-Ching Chuang

Molecules, Vol 18, Iss 3, Pp 2611-

Synthesis of α,β-Dehydroamino Acid Derivatives

2013 Volume 2622

Abstract	The direct nucleophilic addition of alkyl amines to the α(δ')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate α,β-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the α-selective nucleophilic conjugate addition to conjugated dimethyl (E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.
Keywords	α-Michael addition ; conjugated enyne ; dehydroamino acids ; Organic chemistry ; QD241-441
Language	English
Publishing date	2013-02-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation.

Zou, Wei / Wu, An-Tai / Bhasin, Milan / Sandbhor, Mahendra / Wu, Shih-Hsiung

The Journal of organic chemistry

2007 Volume 72, Issue 7, Page(s) 2686–2689

Abstract: ... glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good ...

Abstract	6-nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.
MeSH term(s)	Amination ; Glycosides/chemistry ; Hydroxylation ; Indoles/chemical synthesis ; Indoles/chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oxidation-Reduction
Chemical Substances	Glycosides ; Indoles ; 2-oxindole (0S9338U62H) ; indoline (6DPT9AB2NK)
Language	English
Publishing date	2007-03-09
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo070014o
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Zs.A 4473: Show issues

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Jg. 1995 - 2021: Lesesall (2.OG)
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Article: New stenurothripid thrips from mid-Cretaceous Kachin amber (Thysanoptera, Stenurothripidae).

Guo, Dawei / Engel, Michael S / Shih, Chungkun / Ren, Dong

ZooKeys

2024 Volume 1192, Page(s) 197–212

Abstract: Hitherto, only two species of the thysanopteran suborder Terebrantia have been reported from mid-Cretaceous Kachin amber (Myanmar). This is here expanded through the discovery of two new genera and species, described and figured ... ...

Abstract	Hitherto, only two species of the thysanopteran suborder Terebrantia have been reported from mid-Cretaceous Kachin amber (Myanmar). This is here expanded through the discovery of two new genera and species, described and figured as
Language	English
Publishing date	2024-02-21
Publishing country	Bulgaria
Document type	Journal Article
ZDB-ID	2445640-8
ISSN	1313-2970 ; 1313-2989
ISSN (online)	1313-2970
ISSN	1313-2989
DOI	10.3897/zookeys.1192.117754
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Article ; Online: Comparing botulinum toxin and 4-duct ligation for Sialorrhea in children - A systematic review.

Ha, Tu-Anh N / Shih, Michael C / Lambert, Elton M

American journal of otolaryngology

2023 Volume 45, Issue 2, Page(s) 104119

Abstract: Introduction: Sialorrhea or drooling can result in physical and psychosocial complications, such as aspiration and social isolation. Treatment options include botulinum toxin into the salivary glands and 4-duct ligation (i.e., simultaneous ligation of ... ...

Abstract	Introduction: Sialorrhea or drooling can result in physical and psychosocial complications, such as aspiration and social isolation. Treatment options include botulinum toxin into the salivary glands and 4-duct ligation (i.e., simultaneous ligation of the bilateral parotid and submandibular ducts). This systematic review aimed to compare the efficacy and complication rates of botulinum toxin and 4-duct ligation for the treatment of drooling in children. Methods: Following PRISMA guidelines, PubMed, Embase, Web of Science, and Cochrane Library were searched from inception through June 17, 2021 for studies examining the efficacy of botulinum toxin or 4-duct ligation for drooling in children. Data were summarized by pooled counts, percentages, and means. Complication rates were compared by a chi-squared test. Results: A total of 22 studies (n = 606) examining botulinum toxin and 5 studies (n = 124) examining 4-duct ligation were included. From 12 botulinum toxin studies (n = 211), mean drooling frequency and severity scores was 7.5 at baseline. Mean difference from baseline was -2.6 (n = 92) at 4 weeks follow-up, -2.1 at 8 weeks (n = 41), -2.1 at 12 weeks (n = 56), and - 2.1 at 16 weeks (n = 58). From 4 4-duct ligation studies (n = 103), mean baseline drooling frequency and severity score was 8.4. Mean difference was -3.7 at mean follow-up of 35.6 months (n = 103). Eighteen botulinum studies (n = 343) recorded 53 (15.5 %) complications, including thickened saliva (n = 9), dysphagia (n = 4), and cheek abscesses (n = 4). Four 4-duct ligation studies (n = 108) recorded 25 (23.1 %) complications, including parotid gland swelling (n = 4), aspiration pneumonia (n = 3), and oxygen desaturation (n = 3). There was no statistically significant difference in complication rates between botulinum toxin and four-duct ligation (p = 0.065). Conclusion: Botulinum toxin injection and 4-duct ligation are both effective in improving sialorrhea in children and have comparable complication rates.
MeSH term(s)	Child ; Humans ; Sialorrhea/drug therapy ; Sialorrhea/etiology ; Sialorrhea/surgery ; Botulinum Toxins, Type A/therapeutic use ; Parotid Gland/surgery ; Saliva ; Salivary Ducts ; Treatment Outcome ; Submandibular Gland
Chemical Substances	Botulinum Toxins, Type A (EC 3.4.24.69)
Language	English
Publishing date	2023-11-24
Publishing country	United States
Document type	Systematic Review ; Journal Article
ZDB-ID	604541-8
ISSN	1532-818X ; 0196-0709
ISSN (online)	1532-818X
ISSN	0196-0709
DOI	10.1016/j.amjoto.2023.104119
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Zs.A 1637: Show issues

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Article: New Earwigs from the Middle Jurassic Jiulongshan Formation of Northeastern China (Dermaptera).

Yin, Yuqing / Shih, Chungkun / Engel, Michael S / Ren, Dong

Insects

2023 Volume 14, Issue 7

Abstract: Two new genera and species of Dermaptera are described from the Middle Jurassic Jiulongshan Formation of Daohugou, Inner Mongolia, China: ...

Abstract	Two new genera and species of Dermaptera are described from the Middle Jurassic Jiulongshan Formation of Daohugou, Inner Mongolia, China:
Language	English
Publishing date	2023-07-07
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2662247-6
ISSN	2075-4450
ISSN	2075-4450
DOI	10.3390/insects14070614
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