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Publications (6 of 6) Show all publications
Xie, S., Zhou, J., Chen, X., Kong, N., Fan, Y., Hammer, G., . . . Yan, M. (2019). A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction. MATERIALS CHEMISTRY FRONTIERS, 3(2), 251-256
Open this publication in new window or tab >>A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction
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2019 (English)In: MATERIALS CHEMISTRY FRONTIERS, ISSN 2052-1537, Vol. 3, no 2, p. 251-256Article in journal (Refereed) Published
Abstract [en]

In a tri-component reaction, an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine react readily at room temperature without any catalysts in solvents including aqueous conditions to yield a stable amidine conjugate. The versatility of this reaction is demonstrated in the conjugation of an amino acid without prior protection of the carboxyl group, and in the synthesis of antibiotic-nanoparticle conjugates.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY, 2019
National Category
Materials Chemistry
Identifiers
urn:nbn:se:kth:diva-244534 (URN)10.1039/c8qm00516h (DOI)000457644400009 ()2-s2.0-85060918688 (Scopus ID)
Note

QC 20190403

Available from: 2019-04-03 Created: 2019-04-03 Last updated: 2019-06-25Bibliographically approved
Zhang, Y., Xie, S., Yan, M. & Ramström, O. (2019). Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones. Molecular Catalysis, 470, 138-144
Open this publication in new window or tab >>Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones
2019 (English)In: Molecular Catalysis, ISSN 2468-8231, Vol. 470, p. 138-144Article in journal (Refereed) Published
Abstract [en]

AAsymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of beta-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbonylations operating in cascade. Various N-aryloxazolidinone derivatives were obtained in high yields and good enantiopurities.

Place, publisher, year, edition, pages
Elsevier, 2019
Keywords
Asymmetric synthesis, Candida Antarctica lipase B, Cascade alkoxycarbonylation, Dynamic kinetic resolution, Oxazolidinone, Candida, Isomers, Ruthenium, Yeast, Alkoxycarbonylation, Oxazolidinones, Kinetics
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-252525 (URN)10.1016/j.mcat.2019.03.020 (DOI)000469906600017 ()2-s2.0-85063965626 (Scopus ID)
Note

QC 20190613

Available from: 2019-06-13 Created: 2019-06-13 Last updated: 2019-06-25Bibliographically approved
Xie, S., Manuguri, S., Ramström, O. & Yan, M. (2019). Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone. Chemistry - An Asian Journal, 14(6), 910-916
Open this publication in new window or tab >>Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone
2019 (English)In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, no 6, p. 910-916Article in journal (Refereed) Published
Abstract [en]

The fluorescence properties of AIE-active N-amidinated fluoroquinolones, efficiently obtained by a perfluoroaryl azide-aldehyde-amine reaction, have been studied. The fluorophores were discovered to elicit a highly sensitive fluorescence quenching response towards guest molecules with hydrogen-bond-donating ability. This effect was evaluated in a range of protic/aprotic solvents with different H-bonding capabilities, and also in aqueous media. The influence of acid/base was furthermore addressed. The hydrogen-bonding interactions were studied by IR, NMR, UV/Vis and time-resolved fluorescence decay, revealing their roles in quenching of the fluorescence emission. Due to the pronounced quenching property of water, the N-amidinated fluoroquinolones could be utilized as fluorescent probes for quantifying trace amount of water in organic solvents.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019
Keywords
aggregation-induced emission, fluorescence quenching, fluoroquinolones, hydrogen bonds, water sensors
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-248338 (URN)10.1002/asia.201801916 (DOI)000461836500032 ()30762939 (PubMedID)2-s2.0-85062327816 (Scopus ID)
Note

QC 20190408

Available from: 2019-04-08 Created: 2019-04-08 Last updated: 2019-04-08Bibliographically approved
Sundhoro, M., Jeon, S., Park, J., Ramström, O. & Yan, M. (2017). Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction. Angewandte Chemie International Edition, 56(40), 12117-12121
Open this publication in new window or tab >>Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
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2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 40, p. 12117-12121Article in journal (Refereed) Published
Abstract [en]

We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18m(-1)s(-1) was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH, 2017
Keywords
bioconjugation, bioorthogonal reactions, metabolic labelling, perfluoroaryl azides, Staudinger reaction
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-215444 (URN)10.1002/anie.201705346 (DOI)000411267800010 ()28796447 (PubMedID)
Note

QC 20171019

Available from: 2017-10-19 Created: 2017-10-19 Last updated: 2017-10-19Bibliographically approved
Yan, M. (2017). Synthesis and photocatalytic activity of covalently conjugated three-dimensional pristine graphene-TiO2 nanocomposite. Paper presented at 253rd National Meeting of the American-Chemical-Society (ACS) on Advanced Materials, Technologies, Systems, and Processes, APR 02-06, 2017, San Francisco, CA. Abstract of Papers of the American Chemical Society, 253
Open this publication in new window or tab >>Synthesis and photocatalytic activity of covalently conjugated three-dimensional pristine graphene-TiO2 nanocomposite
2017 (English)In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 253Article in journal, Meeting abstract (Other academic) Published
Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2017
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-242596 (URN)000430569106088 ()
Conference
253rd National Meeting of the American-Chemical-Society (ACS) on Advanced Materials, Technologies, Systems, and Processes, APR 02-06, 2017, San Francisco, CA
Note

QC 20190226

Available from: 2019-02-26 Created: 2019-02-26 Last updated: 2019-02-26Bibliographically approved
Kong, N., Shimpi, M. R., Park, J., Ramström, O. & Yan, M. (2015). Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides (vol 405, pg 33, 2015). Carbohydrate Research, 412, 80-80
Open this publication in new window or tab >>Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides (vol 405, pg 33, 2015)
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2015 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 412, p. 80-80Article in journal (Refereed) Published
Place, publisher, year, edition, pages
ELSEVIER SCI LTD, 2015
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-243662 (URN)10.1016/j.carres.2015.03.013 (DOI)000357542000012 ()2-s2.0-84934753187 (Scopus ID)
Note

QC 20190304

Available from: 2019-03-04 Created: 2019-03-04 Last updated: 2019-03-04Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0003-1121-4007

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