PMID- 31420932
OWN - NLM
STAT- MEDLINE
DCOM- 20201028
LR  - 20231014
IS  - 1521-3773 (Electronic)
IS  - 1433-7851 (Print)
IS  - 1433-7851 (Linking)
VI  - 58
IP  - 41
DP  - 2019 Oct 7
TI  - Zinc Substitution of Cobalt in Vitamin B(12) : Zincobyric acid and Zincobalamin 
      as Luminescent Structural B(12) -Mimics.
PG  - 14568-14572
LID - 10.1002/anie.201908428 [doi]
AB  - Replacing the central cobalt ion of vitamin B(12) by other metals has been a 
      long-held aspiration within the B(12) -field. Herein, we describe the synthesis 
      from hydrogenobyric acid of zincobyric acid (Znby) and zincobalamin (Znbl), the 
      Zn-analogues of the natural cobalt-corrins cobyric acid and vitamin B(12) , 
      respectively. The solution structures of Znby and Znbl were studied by 
      NMR-spectroscopy. Single crystals of Znby were produced, providing the first 
      X-ray crystallographic structure of a zinc corrin. The structures of Znby and of 
      computationally generated Znbl were found to resemble the corresponding Co(II) 
      -corrins, making such Zn-corrins potentially useful for investigations of B(12) 
      -dependent processes. The singlet excited state of Znby had a short life-time, 
      limited by rapid intersystem crossing to the triplet state. Znby allowed the 
      unprecedented observation of a corrin triplet (E(T) =190 kJ mol(-1) ) and was 
      found to be an excellent photo-sensitizer for (1) O(2) (Phi(Delta) =0.70).
CI  - (c) 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
FAU - Kieninger, Christoph
AU  - Kieninger C
AUID- ORCID: 0000-0002-2808-6534
AD  - Institute of Organic Chemistry and Center for Molecular Biosciences (CMBI), 
      University of Innsbruck, 6020, Innsbruck, Austria.
FAU - Baker, Joseph A
AU  - Baker JA
AUID- ORCID: 0000-0002-7603-6304
AD  - School of Biosciences, University of Kent, Canterbury, CT2 7NJ, UK.
FAU - Podewitz, Maren
AU  - Podewitz M
AUID- ORCID: 0000-0001-7256-1219
AD  - Institute of General, Inorganic and Theoretical Chemistry and Center for 
      Molecular Biosciences (CMBI), University of Innsbruck, 6020, Innsbruck, Austria.
FAU - Wurst, Klaus
AU  - Wurst K
AUID- ORCID: 0000-0002-8774-9051
AD  - Institute of General, Inorganic and Theoretical Chemistry and Center for 
      Molecular Biosciences (CMBI), University of Innsbruck, 6020, Innsbruck, Austria.
FAU - Jockusch, Steffen
AU  - Jockusch S
AD  - Department of Chemistry, Columbia University, New York, USA.
FAU - Lawrence, Andrew D
AU  - Lawrence AD
AUID- ORCID: 0000-0002-5853-5409
AD  - School of Biosciences, University of Kent, Canterbury, CT2 7NJ, UK.
FAU - Deery, Evelyne
AU  - Deery E
AD  - School of Biosciences, University of Kent, Canterbury, CT2 7NJ, UK.
FAU - Gruber, Karl
AU  - Gruber K
AD  - Institute for Molecular Biosciences, University of, Graz, Austria.
FAU - Liedl, Klaus R
AU  - Liedl KR
AUID- ORCID: 0000-0002-0985-2299
AD  - Institute of General, Inorganic and Theoretical Chemistry and Center for 
      Molecular Biosciences (CMBI), University of Innsbruck, 6020, Innsbruck, Austria.
FAU - Warren, Martin J
AU  - Warren MJ
AUID- ORCID: 0000-0002-6028-6456
AD  - School of Biosciences, University of Kent, Canterbury, CT2 7NJ, UK.
FAU - Krautler, Bernhard
AU  - Krautler B
AUID- ORCID: 0000-0002-2222-0587
AD  - Institute of Organic Chemistry and Center for Molecular Biosciences (CMBI), 
      University of Innsbruck, 6020, Innsbruck, Austria.
LA  - eng
GR  - M 2005/FWF_/Austrian Science Fund FWF/Austria
GR  - M-2005/Osterreichische Forschungsforderungsgesellschaft/International
GR  - BB/S002197/1/BB_/Biotechnology and Biological Sciences Research Council/United 
      Kingdom
GR  - BB/K009249/1/BB_/Biotechnology and Biological Sciences Research Council/United 
      Kingdom
GR  - BB/L010208//BB_/Biotechnology and Biological Sciences Research Council/United 
      Kingdom
GR  - P 28892/FWF_/Austrian Science Fund FWF/Austria
GR  - P-28892/Osterreichische Forschungsforderungsgesellschaft/International
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20190904
PL  - Germany
TA  - Angew Chem Int Ed Engl
JT  - Angewandte Chemie (International ed. in English)
JID - 0370543
RN  - 3G0H8C9362 (Cobalt)
RN  - J41CSQ7QDS (Zinc)
RN  - P6YC3EG204 (Vitamin B 12)
SB  - IM
MH  - Cobalt/*chemistry
MH  - Luminescence
MH  - Models, Molecular
MH  - Molecular Mimicry
MH  - Molecular Structure
MH  - Thermodynamics
MH  - Vitamin B 12/*analogs & derivatives/*chemistry
MH  - Zinc/*chemistry
PMC - PMC6790578
OTO - NOTNLM
OT  - X-ray structure
OT  - cobalamins
OT  - photochemistry
OT  - transition metal
OT  - vitamin
COIS- The authors declare no conflict of interest.
EDAT- 2019/08/20 06:00
MHDA- 2020/10/29 06:00
PMCR- 2019/10/14
CRDT- 2019/08/18 06:00
PHST- 2019/07/07 00:00 [received]
PHST- 2019/08/20 06:00 [pubmed]
PHST- 2020/10/29 06:00 [medline]
PHST- 2019/08/18 06:00 [entrez]
PHST- 2019/10/14 00:00 [pmc-release]
AID - ANIE201908428 [pii]
AID - 10.1002/anie.201908428 [doi]
PST - ppublish
SO  - Angew Chem Int Ed Engl. 2019 Oct 7;58(41):14568-14572. doi: 
      10.1002/anie.201908428. Epub 2019 Sep 4.