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Xie X.,State Key Laboratory of Bioorganic and Natural Products Chemistry | Li F.,State Key Laboratory of Bioorganic and Natural Products Chemistry | Li F.,The Interdisciplinary Center | Wang Y.,CAS Institut Pasteur of Shanghai | And 8 more authors.
Autophagy | Year: 2015

The autophagy receptor CALCOCO2/NDP52 functions as a bridging adaptor and plays an essential role in the selective autophagic degradation of invading pathogens by specifically recognizing ubiquitin-coated intracellular pathogens and subsequently targeting them to the autophagic machinery; thereby it is required for innate immune defense against a range of infectious pathogens in mammals. However, the mechanistic basis underlying CALCOCO2- mediated specific recognition of ubiqutinated pathogens is still unknown. Here, using biochemical and structural analyses, we demonstrated that the cargo-binding region of CALCOCO2 contains a dynamic unconventional zinc finger as well as a C2H2-type zinc-finger, and only the C2H2-type zinc finger specifically recognizes mono-ubiquitin or polyubiquitin chains. In addition to elucidating the specific ubiquitin recognition mechanism of CALCOCO2, the structure of the CALCOCO2 C2H2-type zinc finger in complex with mono-ubiquitin also uncovers a unique zinc finger-binding mode for ubiquitin. Our findings provide mechanistic insight into how CALCOCO2 targets ubiquitin-decorated pathogens for autophagic degradations. © 2015 Taylor and Francis Group, LLC.


Fu R.,Xiamen University | Ye J.-L.,Xiamen University | Dai X.-J.,Xiamen University | Ruan Y.-P.,Xiamen University | And 2 more authors.
Journal of Organic Chemistry | Year: 2010

Full details of the convergent synthetic approach to awajanomycin, and the first total syntheses of the marine natural product (+)-awajanomycin (1) and its C-11 epimer 38 by an improved 13-step approach, are described. The key elements of the synthetic strategy resided in the use of (R)-18 as the chiral building block to construct the γ-lactone-δ-lactam core 3 and cross-olefin metathesis as the key reaction to couple the latter with the allylic alcohol segment (R- or S-4). The efficient construction of the core 3 was realized by taking advantage of the inherent multiple reactivities of the chiral building block (R)-18. A highly diastereoselective one-pot transformation of 6 to 26 was achieved in a one stone four birds manner. On the other hand, enantioselective synthesis of both enantiomers of the segment 4 has been undertaken by an alternative and more efficient two-step procedure. Both awajanomycin (1) and 11-epi-awajanomycin 38 have been synthesized with overall yields of 3.8% and 3.6%, respectively. Quantum chemical calculations were undertaken to reveal the low reactivity of compound 27 toward methoxycarbonylation and to get an insight into the favored conformations of the intermediates 25-27. In addition, the geometry of the side product 39 arising from the homocoupling of the allylic alcohol moiety 4 was revised as E, and an unusual cyclopropanation reaction was discovered. © 2010 American Chemical Society.


Liu X.-K.,Xiamen University | Ye J.-L.,Xiamen University | Ruan Y.-P.,Xiamen University | Li Y.-X.,Xiamen University | And 2 more authors.
Journal of Organic Chemistry | Year: 2013

An efficient synthesis of the Stemona alkaloid (-)-sessilifoliamide J (1) in 12 steps and 7.7% overall yield from the known building block 8 is presented. The synthesis features the Corey lactonization reaction and a highly diastereoselective α-methylation reaction to build the spirolactone moiety. © 2012 American Chemical Society.


Ruan S.-T.,Xiamen University | Luo J.-M.,Xiamen University | Du Y.,Xiamen University | Huang P.-Q.,Xiamen University | Huang P.-Q.,State Key Laboratory of Bioorganic and Natural Products Chemistry
Organic Letters | Year: 2011

Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert- butyldimethylsilyloxy)furan (TBSOF, 1) with (R S)- or (S S)-t-BS-imines (3) furnished 5-aminoalkylbutenolides 7a-k in 75-87% yields with anti/syn ratios ranging from 75:25 to 97:3. Butenolides 7a-f,k were readily converted into substituted lactones 8 and 5 and 6-substituted 5-hydroxypiperidin-2-ones 11a-g, which are, in turn, key intermediates for the synthesis of many bioactive compounds. © 2011 American Chemical Society.


Tuo S.-C.,Xiamen University | Ye J.-L.,Xiamen University | Wang Ai.-E.,Xiamen University | Huang S.-Y.,Xiamen University | And 2 more authors.
Organic Letters | Year: 2011

A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI2-mediated coupling lactonization. The absolute configuration of the natural sessilifoliamide J was established. © 2011 American Chemical Society.


Lan H.-Q.,Xiamen University | Ye J.-L.,Xiamen University | Wang A.-E.,Xiamen University | Ruan Y.-P.,Xiamen University | And 2 more authors.
Chemistry - A European Journal | Year: 2011

By using a methyl tetramate derivative (R)- or (S)-9 as a novel chiral building block, a direct, flexible, and highly enantioselective approach to methyl (R)- or (S)-5-alkyltetramates (2) is disclosed. Among the synthesized methyl 5-alkyltetramates 2, methyl 5-methyltetramate (2a) is found in cytotoxic mirabimide E (4) and dysideapyrrolidone (5), and methyl 5-benzyltetramate (2g) is a substructure in the potent antineoplastic dolastatin 15 (3). On the basis of this method, the first asymmetric synthesis of the antimitotic tetrapeptide belamide A (7) has been achieved in seven steps from (S)-9, with an overall yield of 23.8%. Not only have the structure and absolute configuration of (+)-belamide A (7) been confirmed, but also the solvent used for recording the 13C NMR spectrum, the 13C NMR spectrum data correlation, and optical rotation data of natural belamide A (7) have been revised. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA.


Lan H.-Q.,Xiamen University | Ruan Y.-P.,Xiamen University | Huang P.-Q.,Xiamen University | Huang P.-Q.,State Key Laboratory of Bioorganic and Natural Products Chemistry
Chemical Communications | Year: 2010

Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3- methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S. © 2010 The Royal Society of Chemistry.


Luo S.-P.,Xiamen University | Guo L.-D.,Xiamen University | Gao L.-H.,Xiamen University | Li S.,Xiamen University | And 2 more authors.
Chemistry - A European Journal | Year: 2013

Three keys to success: A concise method for the construction of a tricyclic substructure (2) of haliclonin A (1) in racemic form is described (see figure). This synthesis features a new Pd-mediated chemoselective carbonyl-enone coupling reaction, an organocatalytic reaction, and a ring-closing metathesis reaction for the construction of the macrocyclic ring as key steps. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Yang R.-F.,Xiamen University | Huang P.-Q.,Xiamen University | Huang P.-Q.,State Key Laboratory of Bioorganic and Natural Products Chemistry
Chemistry - A European Journal | Year: 2010

Figure Presented A powerful chiral building block: A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block (R)-1(see scheme), and features a tandem Horner-WadsworthEmmons-aza-Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of the necessary functionality for further elaboration into sarain A. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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