PMID- 27739022
OWN - NLM
STAT- MEDLINE
DCOM- 20190606
LR  - 20190606
IS  - 1879-1123 (Electronic)
IS  - 1044-0305 (Linking)
VI  - 28
IP  - 2
DP  - 2017 Feb
TI  - Enantiomeric Excess Determination for Monosaccharides Using Chiral Transmission 
      to Cold Gas-Phase Tryptophan in Ultraviolet Photodissociation.
PG  - 224-228
LID - 10.1007/s13361-016-1519-5 [doi]
AB  - Chiral transmission between monosaccharides and amino acids via photodissociation 
      in the gas phase was examined using a tandem mass spectrometer fitted with an 
      electrospray ionization source and a cold ion trap in order to investigate the 
      origin of the homochirality of biomolecules in molecular clouds. Ultraviolet 
      photodissociation mass spectra of cold gas-phase noncovalent complexes of the 
      monosaccharide enantiomers glucose (Glc) and galactose (Gal) with protonated 
      L-tryptophan H(+)(L-Trp) were obtained by photoexcitation of the indole ring of 
      L-Trp. L-Trp dissociated via C(alpha)-C(beta) bond cleavage when noncovalently complexed 
      with D-Glc; however, no dissociation of L-Trp occurred in the homochiral 
      H(+)(L-Trp)(L-Glc) noncovalent complex, where the energy absorbed by L-Trp was 
      released through the evaporation of L-Glc. This enantioselective 
      photodissociation of Trp was due to the transmission of chirality from Glc to Trp 
      via photodissociation in the gas-phase noncovalent complexes, and was applied to 
      the quantitative chiral analysis of monosaccharides. The enantiomeric excess of 
      monosaccharides in solution could be determined by measuring the relative 
      abundance of the two product ions in a single photodissociation mass spectrum of 
      the cold gas-phase noncovalent complex with H(+)(L-Trp), and by referring to the 
      linear relationships derived in this work. Graphical Abstract ᅟ.
FAU - Fujihara, Akimasa
AU  - Fujihara A
AD  - Department of Chemistry, Osaka Prefecture University, Sakai, Osaka, 599-8531, 
      Japan. fujihara@c.s.osakafu-u.ac.jp.
FAU - Maeda, Naoto
AU  - Maeda N
AD  - Department of Chemistry, Osaka Prefecture University, Sakai, Osaka, 599-8531, 
      Japan.
FAU - Doan, Thuc N
AU  - Doan TN
AD  - Department of Chemistry, Osaka Prefecture University, Sakai, Osaka, 599-8531, 
      Japan.
FAU - Hayakawa, Shigeo
AU  - Hayakawa S
AD  - Department of Chemistry, Osaka Prefecture University, Sakai, Osaka, 599-8531, 
      Japan.
LA  - eng
PT  - Journal Article
DEP - 20161013
PL  - United States
TA  - J Am Soc Mass Spectrom
JT  - Journal of the American Society for Mass Spectrometry
JID - 9010412
RN  - 0 (Gases)
RN  - 0 (Monosaccharides)
RN  - 8DUH1N11BX (Tryptophan)
RN  - IY9XDZ35W2 (Glucose)
RN  - X2RN3Q8DNE (Galactose)
SB  - IM
MH  - Galactose/analysis/chemistry
MH  - Gases
MH  - Glucose/analysis/chemistry
MH  - Monosaccharides/*analysis/*chemistry/radiation effects
MH  - Photochemical Processes
MH  - Spectrometry, Mass, Electrospray Ionization/*methods
MH  - Stereoisomerism
MH  - Tandem Mass Spectrometry
MH  - Tryptophan/*chemistry
MH  - Ultraviolet Rays
OTO - NOTNLM
OT  - Chiral recognition
OT  - Enantioselective
OT  - Gas-phase cluster
OT  - Homochirality
OT  - Molecular cloud
OT  - Noncovalent complex
OT  - Optical purity
EDAT- 2016/10/16 06:00
MHDA- 2019/06/07 06:00
CRDT- 2016/10/15 06:00
PHST- 2016/08/05 00:00 [received]
PHST- 2016/10/01 00:00 [accepted]
PHST- 2016/09/27 00:00 [revised]
PHST- 2016/10/16 06:00 [pubmed]
PHST- 2019/06/07 06:00 [medline]
PHST- 2016/10/15 06:00 [entrez]
AID - 10.1007/s13361-016-1519-5 [pii]
AID - 10.1007/s13361-016-1519-5 [doi]
PST - ppublish
SO  - J Am Soc Mass Spectrom. 2017 Feb;28(2):224-228. doi: 10.1007/s13361-016-1519-5. 
      Epub 2016 Oct 13.