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  1. Article ; Online: Approaches to Cyclophane-Types of Cyclopeptide Alkaloids.

    Wang, Yuanhao / Joullié, Madeleine M

    Chemical record (New York, N.Y.)

    2021  Volume 21, Issue 4, Page(s) 906–923

    Abstract: The cyclopeptide alkaloids are cyclic depsipeptides incorporating cyclophanes with polyamide units 13-, 14- and 15-membered macrocyclic systems. Although various pharmacological activities have been ascribed to cyclopeptide alkaloids from plants of the ... ...

    Abstract The cyclopeptide alkaloids are cyclic depsipeptides incorporating cyclophanes with polyamide units 13-, 14- and 15-membered macrocyclic systems. Although various pharmacological activities have been ascribed to cyclopeptide alkaloids from plants of the Rhamnacea family, these studies have been hampered by their low availability due to the lack of reasonable amounts distributed in nature. Therefore, novel and efficient synthetic approaches should be an important aim, which inspired us to examine how to diversely construct the unique structures of this type of natural products. In this account, several typical strategies are presented in terms of efficient, stereocontrolled and regioselective synthesis of cyclopeptide alkaloids.
    MeSH term(s) Alkaloids/chemical synthesis ; Alkaloids/chemistry ; Biological Products/chemical synthesis ; Biological Products/chemistry ; Macrocyclic Compounds/chemistry ; Molecular Conformation ; Peptides, Cyclic/chemical synthesis ; Peptides, Cyclic/chemistry ; Rhamnaceae/chemistry ; Stereoisomerism
    Chemical Substances Alkaloids ; Biological Products ; Macrocyclic Compounds ; Peptides, Cyclic
    Language English
    Publishing date 2021-03-03
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 2044646-9
    ISSN 1528-0691 ; 1527-8999
    ISSN (online) 1528-0691
    ISSN 1527-8999
    DOI 10.1002/tcr.202100017
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Total synthesis of the reported structure of ceanothine D

    Lee, Jisun / Joullié, Madeleine M

    Chemical science

    2018  Volume 9, Issue 9, Page(s) 2432–2436

    Abstract: The first total synthesis of the reported structure of ceanothine D, a cyclopeptide alkaloid found in red root, was achieved using a highly convergent synthetic strategy. Highlights of the synthesis include the first concomitant macrocyclization and ... ...

    Abstract The first total synthesis of the reported structure of ceanothine D, a cyclopeptide alkaloid found in red root, was achieved using a highly convergent synthetic strategy. Highlights of the synthesis include the first concomitant macrocyclization and formation of the unique chiral tertiary alkyl-aryl ether bond with complete regio- and stereo-control in the presence of a sensitive
    Language English
    Publishing date 2018-01-31
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/c8sc00234g
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Joining Forces: Fermentation and Organic Synthesis for the Production of Complex Heterocycles.

    Gober, Claire M / Joullié, Madeleine M

    The Journal of organic chemistry

    2016  Volume 81, Issue 21, Page(s) 10136–10144

    Abstract: Commercial application of many promising heterocyclic natural products is limited by their natural abundance. While organic synthesis provides access to many natural products, total synthesis of numerous complex molecules is not economically feasible. In ...

    Abstract Commercial application of many promising heterocyclic natural products is limited by their natural abundance. While organic synthesis provides access to many natural products, total synthesis of numerous complex molecules is not economically feasible. In recent years, the combination of fermentation and organic synthesis has provided a new route for the production of complex heterocycles that are inaccessible by typical synthetic methods. This JOCSynopsis will review examples of how this union of disciplines has overcome obstacles in both academia and industry.
    MeSH term(s) Biological Products/chemical synthesis ; Biological Products/metabolism ; Fermentation ; Heterocyclic Compounds/chemical synthesis ; Organic Chemicals/chemical synthesis
    Chemical Substances Biological Products ; Heterocyclic Compounds ; Organic Chemicals
    Language English
    Publishing date 2016-07-28
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, Non-P.H.S. ; Review
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.6b01308
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.A 4473: Show issues Location:
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    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  4. Article ; Online: A Transannular Rearrangement Reaction of a Pyrroloindoline Diketopiperazine.

    Yan, Qiao / Carroll, Patrick J / Gau, Michael R / Winkler, Jeffrey D / Joullié, Madeleine M

    Organic letters

    2019  Volume 21, Issue 17, Page(s) 6619–6623

    Abstract: Oxaline, glandicoline, and meleagrin contain a unique triazaspirocyclic structure. Attracted by their biological activities, we attempted a novel strategy, mimicking a proposed biosynthetic pathway for glandicoline B ... ...

    Abstract Oxaline, glandicoline, and meleagrin contain a unique triazaspirocyclic structure. Attracted by their biological activities, we attempted a novel strategy, mimicking a proposed biosynthetic pathway for glandicoline B in
    Language English
    Publishing date 2019-08-15
    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.9b02084
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  5. Article: Triazaspirocycles: Occurrence, Synthesis, and Applications.

    Gober, Claire M / Carroll, Patrick J / Joullié, Madeleine M

    Mini-reviews in organic chemistry

    2016  Volume 13, Issue 2, Page(s) 126–142

    Abstract: Natural products bearing a triazaspirocyclic motif have received significant attention in recent years. These compounds, which feature three nitrogen atoms attached to one quaternary carbon forming a spirocyclic scaffold, exhibit a wide range of ... ...

    Abstract Natural products bearing a triazaspirocyclic motif have received significant attention in recent years. These compounds, which feature three nitrogen atoms attached to one quaternary carbon forming a spirocyclic scaffold, exhibit a wide range of biological activity and have promising applications in materials as well as in drug discovery. In this review article, we will discuss triazaspirocycles in Nature, their biological activity, and applications. Methods for the synthesis of triazaspirocycles as well as the reactivity of triazaspirocyclic scaffolds will be reviewed.
    Language English
    Publishing date 2016-06-06
    Publishing country United Arab Emirates
    Document type Journal Article
    ISSN 1570-193X
    ISSN 1570-193X
    DOI 10.2174/1570193X13666160225001001
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: A Transannular Rearrangement Reaction of a Pyrroloindoline Diketopiperazine

    Yan, Qiao / Carroll, Patrick J / Gau, Michael R / Winkler, Jeffrey D / Joullié, Madeleine M

    Organic letters. 2019 Aug. 15, v. 21, no. 17

    2019  

    Abstract: Oxaline, glandicoline, and meleagrin contain a unique triazaspirocyclic structure. Attracted by their biological activities, we attempted a novel strategy, mimicking a proposed biosynthetic pathway for glandicoline B in Penicillium chrysogenum and ... ...

    Abstract Oxaline, glandicoline, and meleagrin contain a unique triazaspirocyclic structure. Attracted by their biological activities, we attempted a novel strategy, mimicking a proposed biosynthetic pathway for glandicoline B in Penicillium chrysogenum and Penicillium oxalicum and using a transannular rearrangement to the desired triazaspirocycle 15.
    Keywords Penicillium chrysogenum ; Penicillium oxalicum ; bioactive properties ; biochemical pathways ; chemical reactions ; chemical structure ; diketopiperazines
    Language English
    Dates of publication 2019-0815
    Size p. 6619-6623.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b02084
    Database NAL-Catalogue (AGRICOLA)

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  7. Article ; Online: Total synthesis of Lys(3) tamandarin M: a potential affinity ligand.

    Lassen, Kenneth M / Joullié, Madeleine M

    Organic letters

    2010  Volume 12, Issue 22, Page(s) 5306–5309

    Abstract: The synthesis of Lys(3) tamandarin M is described. This analogue can be used as a protein affinity ...

    Abstract The synthesis of Lys(3) tamandarin M is described. This analogue can be used as a protein affinity ligand to probe the mechanism of action of this unique class of molecules.
    MeSH term(s) Catalysis ; Depsipeptides/chemical synthesis ; Depsipeptides/chemistry ; Molecular Structure ; Trimethylsilyl Compounds/chemical synthesis ; Trimethylsilyl Compounds/chemistry
    Chemical Substances Depsipeptides ; Lys(3) tamandarin M ; Trimethylsilyl Compounds ; tamandarin A ; tamandarin B ; tamandarin M ; didemnins (4LSZ9C5HOB)
    Language English
    Publishing date 2010-10-29
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol1024212
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  8. Article ; Online: Possible reason for the unusual regioselectivity in nucleophilic ring opening of trisubstituted aziridines under mildly basic conditions.

    Kelley, Brandon T / Carroll, Patrick / Joullié, Madeleine M

    The Journal of organic chemistry

    2014  Volume 79, Issue 11, Page(s) 5121–5133

    Abstract: 2,2,3-Trisubstituted aziridines are known to undergo ring opening at the more substituted carbon under mildly basic conditions. However, the reason for the formation of the more sterically encumbered product has never been examined. Several ... ...

    Abstract 2,2,3-Trisubstituted aziridines are known to undergo ring opening at the more substituted carbon under mildly basic conditions. However, the reason for the formation of the more sterically encumbered product has never been examined. Several trisubstituted aziridines, with different substitution patterns at the C-2 and C-3 carbons, were synthesized to change the electronics of the aziridine ring system. These changes had no effect on the regioselectivity of the ring-opening reaction. Using the B3LYP/6-31G* DFT basis set it was determined that the transition state for opening at the more substituted carbon proceeds at a lower energy than the transition state at the less substituted carbon.
    MeSH term(s) Aziridines/chemical synthesis ; Aziridines/chemistry ; Models, Molecular ; Quantum Theory ; Stereoisomerism
    Chemical Substances Aziridines ; aziridine (54P5FEX9FH)
    Language English
    Publishing date 2014-06-06
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo5006685
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  9. Article ; Online: Ring opening of a trisubstituted aziridine with amines: regio- and stereoselective formation of substituted 1,2-diamines.

    Kelley, Brandon T / Joullié, Madeleine M

    Organic letters

    2010  Volume 12, Issue 19, Page(s) 4244–4247

    Abstract: The formation of substituted 1,2-diamines via nucleophilic ring opening of a trisubstituted ethynyl aziridine was performed with complete regio- and stereoselective control. Various amines with different levels of nucleophilicity were employed and gave ... ...

    Abstract The formation of substituted 1,2-diamines via nucleophilic ring opening of a trisubstituted ethynyl aziridine was performed with complete regio- and stereoselective control. Various amines with different levels of nucleophilicity were employed and gave similar results. The ring opening reaction is not limited to ethynyl aziridines, as other alkyl trisubstituted aziridines gave the same results. This method allows for the formation of unique vicinal diamines while providing a fully substituted carbon center in a stereoselective manner under mild conditions.
    MeSH term(s) Alkynes/chemistry ; Amines/chemistry ; Amino Acids/chemistry ; Aziridines/chemistry ; Cyclization ; Diamines/chemical synthesis ; Models, Molecular ; Molecular Structure ; Pyrazoles/chemistry ; Stereoisomerism
    Chemical Substances Alkynes ; Amines ; Amino Acids ; Aziridines ; Diamines ; Pyrazoles ; aziridine (54P5FEX9FH)
    Language English
    Publishing date 2010-10-01
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol101584z
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Incorporating Fermentation into Undergraduate Laboratory Courses.

    Gober, Claire / Joullie, Madeleine

    Athens journal of sciences

    2017  Volume 2, Issue 4, Page(s) 257–264

    Abstract: Laboratory courses in universities have a responsibility to introduce current research practices and trends in scientific research to adequately prepare students for work in the field. One such research practice gaining popularity in recent years is that ...

    Abstract Laboratory courses in universities have a responsibility to introduce current research practices and trends in scientific research to adequately prepare students for work in the field. One such research practice gaining popularity in recent years is that of green chemistry. Since the 1960s, increasing concern over the release of toxic chemicals into the environment has led to a push for more environmentally responsible chemistry. A growing faction of chemists has begun to adopt methods to eliminate chemical waste and support green chemistry. Fermentation is an ideal technique to demonstrate environmentally sustainable chemistry in an undergraduate laboratory class. Fermentation of complex natural products, as opposed to traditional organic synthesis, is beneficial as it supports a number of principles of green chemistry; it is conducted at ambient temperature and pressure, uses inexpensive and innocuous materials, makes use of renewable resources, and does not require a fume hood. Skills implemented during fermentation can be easily taught to upper-level Chemistry and Biochemistry undergraduate students, who typically have limited exposure to complex natural products in their coursework. Such a course would be interdisciplinary in nature, incorporating fungal biology and metabolism as well as organic chemistry. Students would learn a variety of skills, including growth media selection and preparation, inoculation of fungal cultures, extraction of natural products, and purification and characterization of metabolites. Experiments of this nature would allow for discussions of several areas of research: green chemistry, natural products and their application to medicine, identification of functional groups in complex molecules by spectroscopy, and introduction to biochemistry and metabolism. Roquefortine C, a prenylated indole alkaloid readily produced by a variety of species of Penicillia, is an excellent candidate for demonstrating fermentation in a laboratory classroom setting, owing to its ease of purification from other metabolites and its unique structural features.
    Language English
    Publishing date 2017-05-05
    Publishing country Greece
    Document type Journal Article
    ISSN 2241-8466
    ISSN 2241-8466
    Database MEDical Literature Analysis and Retrieval System OnLINE

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