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Nanocrystalline Aggregation of Serine Detected by Electrospray Ionization Mass Spectrometry: Origin of the Stable Homochiral Gas-Phase Serine Octamer

Julian, Ryan R. and Hodyss, Robert and Kinnear, Brian and Jarrold, Martin F. and Beauchamp, J. L. (2002) Nanocrystalline Aggregation of Serine Detected by Electrospray Ionization Mass Spectrometry: Origin of the Stable Homochiral Gas-Phase Serine Octamer. Journal of Physical Chemistry B, 106 (6). pp. 1219-1228. ISSN 1520-6106. doi:10.1021/jp012265l. https://resolver.caltech.edu/CaltechAUTHORS:20170518-144815480

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Abstract

Electrospray ionization sampling of 0.01 M solutions of serine reveals an unusually abundant protonated serine octamer, which demonstrates a strong preference for homochirality. Ion mobility spectra yield an experimental cross section that is consistent with a single “cubic” structure. Density functional theory calculations support experimental observations which suggest that the structure of the serine octamer is closely related to and formed from a small subsection of the crystal structure of anhydrous serine. The formation, bonding, and experimental constraints placed on the serine octamer are discussed in light of the proposed nanocrystalline structure. The mass spectra of the analogous molecules threonine and homoserine exhibit several similar features with that of serine and the likely structures for the octameric species are compared with that of the serine octamer. Finally, implications for the spontaneous symmetry breaking of a racemic mixture and the origin of life are addressed.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jp012265lDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jp012265lPublisherArticle
ORCID:
AuthorORCID
Julian, Ryan R.0000-0003-1580-8355
Hodyss, Robert0000-0002-6523-3660
Beauchamp, J. L.0000-0001-8839-4822
Additional Information:© 2002 American Chemical Society. Received 13 June 2001. Published online 18 January 2002. Published in print 1 February 2002. The authors gratefully acknowledge funding received from the Beckman Institute and the NSF (CHE-9727566).
Funders:
Funding AgencyGrant Number
Caltech Beckman InstituteUNSPECIFIED
NSFCHE-9727566
Issue or Number:6
DOI:10.1021/jp012265l
Record Number:CaltechAUTHORS:20170518-144815480
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170518-144815480
Official Citation:Nanocrystalline Aggregation of Serine Detected by Electrospray Ionization Mass Spectrometry:  Origin of the Stable Homochiral Gas-Phase Serine Octamer Ryan R. Julian, Robert Hodyss, Brian Kinnear, Martin F. Jarrold, and J. L. Beauchamp The Journal of Physical Chemistry B 2002 106 (6), 1219-1228 DOI: 10.1021/jp012265l
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77590
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:19 May 2017 15:54
Last Modified:15 Nov 2021 17:32

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