PMID- 26324178
OWN - NLM
STAT- MEDLINE
DCOM- 20160805
LR  - 20231111
IS  - 2045-2322 (Electronic)
IS  - 2045-2322 (Linking)
VI  - 5
DP  - 2015 Sep 1
TI  - Octanoylation of early intermediates of mycobacterial methylglucose 
      lipopolysaccharides.
PG  - 13610
LID - 10.1038/srep13610 [doi]
LID - 13610
AB  - Mycobacteria synthesize unique intracellular methylglucose lipopolysaccharides 
      (MGLP) proposed to modulate fatty acid metabolism. In addition to the partial 
      esterification of glucose or methylglucose units with short-chain fatty acids, 
      octanoate was invariably detected on the MGLP reducing end. We have identified a 
      novel sugar octanoyltransferase (OctT) that efficiently transfers octanoate to 
      glucosylglycerate (GG) and diglucosylglycerate (DGG), the earliest intermediates 
      in MGLP biosynthesis. Enzymatic studies, synthetic chemistry, NMR spectroscopy 
      and mass spectrometry approaches suggest that, in contrast to the prevailing 
      consensus, octanoate is not esterified to the primary hydroxyl group of glycerate 
      but instead to the C6 OH of the second glucose in DGG. These observations raise 
      important new questions about the MGLP reducing end architecture and about 
      subsequent biosynthetic steps. Functional characterization of this unique 
      octanoyltransferase, whose gene has been proposed to be essential for M. 
      tuberculosis growth, adds new insights into a vital mycobacterial pathway, which 
      may inspire new drug discovery strategies.
FAU - Maranha, Ana
AU  - Maranha A
AD  - CNC - Center for Neuroscience and Cell Biology, University of Coimbra, 3004-517 
      Coimbra, Portugal.
FAU - Moynihan, Patrick J
AU  - Moynihan PJ
AD  - Department of Molecular and Cellular Biology, University of Guelph, Ontario, 
      Canada.
FAU - Miranda, Vanessa
AU  - Miranda V
AD  - ITQB - Instituto de Tecnologia Quimica Biologica, Universidade Nova de Lisboa, 
      Portugal.
FAU - Correia Lourenco, Eva
AU  - Correia Lourenco E
AD  - ITQB - Instituto de Tecnologia Quimica Biologica, Universidade Nova de Lisboa, 
      Portugal.
FAU - Nunes-Costa, Daniela
AU  - Nunes-Costa D
AD  - CNC - Center for Neuroscience and Cell Biology, University of Coimbra, 3004-517 
      Coimbra, Portugal.
FAU - Fraga, Joana S
AU  - Fraga JS
AD  - IBMC - Instituto de Biologia Molecular e Celular, Universidade do Porto, 
      Portugal.
AD  - Instituto de Investigacao e Inovacao em Saude, Universidade do Porto, Portugal.
FAU - Jose Barbosa Pereira, Pedro
AU  - Jose Barbosa Pereira P
AD  - IBMC - Instituto de Biologia Molecular e Celular, Universidade do Porto, 
      Portugal.
AD  - Instituto de Investigacao e Inovacao em Saude, Universidade do Porto, Portugal.
FAU - Macedo-Ribeiro, Sandra
AU  - Macedo-Ribeiro S
AD  - IBMC - Instituto de Biologia Molecular e Celular, Universidade do Porto, 
      Portugal.
AD  - Instituto de Investigacao e Inovacao em Saude, Universidade do Porto, Portugal.
FAU - Ventura, M Rita
AU  - Ventura MR
AD  - ITQB - Instituto de Tecnologia Quimica Biologica, Universidade Nova de Lisboa, 
      Portugal.
FAU - Clarke, Anthony J
AU  - Clarke AJ
AD  - Department of Molecular and Cellular Biology, University of Guelph, Ontario, 
      Canada.
FAU - Empadinhas, Nuno
AU  - Empadinhas N
AD  - CNC - Center for Neuroscience and Cell Biology, University of Coimbra, 3004-517 
      Coimbra, Portugal.
AD  - III/UC- Instituto de Investigacao Interdisciplinar, University of Coimbra, 
      Portugal.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20150901
PL  - England
TA  - Sci Rep
JT  - Scientific reports
JID - 101563288
RN  - 0 (Bacterial Proteins)
RN  - 0 (Fatty Acids)
RN  - 0 (Lipopolysaccharides)
RN  - 0 (Recombinant Proteins)
RN  - EC 2.4.- (Glycosyltransferases)
SB  - IM
MH  - Bacterial Proteins/genetics/metabolism
MH  - Fatty Acids/metabolism
MH  - Glycosylation
MH  - Glycosyltransferases/genetics/metabolism
MH  - Kinetics
MH  - Lipopolysaccharides/*biosynthesis
MH  - Magnetic Resonance Spectroscopy
MH  - Mass Spectrometry
MH  - Mycobacterium/enzymology/*metabolism
MH  - Recombinant Proteins/biosynthesis/chemistry/isolation & purification
MH  - Substrate Specificity
PMC - PMC4555173
EDAT- 2015/09/02 06:00
MHDA- 2016/08/06 06:00
PMCR- 2015/09/01
CRDT- 2015/09/02 06:00
PHST- 2015/05/20 00:00 [received]
PHST- 2015/07/30 00:00 [accepted]
PHST- 2015/09/02 06:00 [entrez]
PHST- 2015/09/02 06:00 [pubmed]
PHST- 2016/08/06 06:00 [medline]
PHST- 2015/09/01 00:00 [pmc-release]
AID - srep13610 [pii]
AID - 10.1038/srep13610 [doi]
PST - epublish
SO  - Sci Rep. 2015 Sep 1;5:13610. doi: 10.1038/srep13610.