Document Detail

Gas-phase reactivity of carboxylic acid functional groups with carbodiimides.
MedLine Citation:
PMID:  23208744     Owner:  NLM     Status:  MEDLINE    
Gas-phase modification of carboxylic acid functionalities is performed via ion/ion reactions with carbodiimide reagents [N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide (CMC) and [3-(3-Ethylcarbodiimide-1-yl)propyl]trimethylaminium (ECPT)]. Gas-phase ion/ion covalent chemistry requires the formation of a long-lived complex. In this instance, the complex is stabilized by an electrostatic interaction between the fixed charge quaternary ammonium group of the carbodiimide reagent cation and the analyte dianion. Subsequent activation results in characteristic loss of an isocyanate derivative from one side of the carbodiimide functionality, a signature for this covalent chemistry. The resulting amide bond is formed on the analyte at the site of the original carboxylic acid. Reactions involving analytes that do not contain available carboxylic acid groups (e.g., they have been converted to sodium salts) or reagents that do not have the carbodiimide functionality do not undergo a covalent reaction. This chemistry is demonstrated using PAMAM generation 0.5 dendrimer, ethylenediaminetetraacetic acid (EDTA), and the model peptide DGAILDGAILD. This work demonstrates the selective gas-phase covalent modification of carboxylic acid functionalities.
Boone M Prentice; Joshua D Gilbert; John R Stutzman; William P Forrest; Scott A McLuckey
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-12-04
Journal Detail:
Title:  Journal of the American Society for Mass Spectrometry     Volume:  24     ISSN:  1879-1123     ISO Abbreviation:  J. Am. Soc. Mass Spectrom.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-01-24     Completed Date:  2013-07-01     Revised Date:  2014-01-09    
Medline Journal Info:
Nlm Unique ID:  9010412     Medline TA:  J Am Soc Mass Spectrom     Country:  United States    
Other Details:
Languages:  eng     Pagination:  30-7     Citation Subset:  IM    
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MeSH Terms
Carbodiimides / chemistry*
Carboxylic Acids / chemistry*
Edetic Acid / chemistry
Gases / chemistry
Ions / chemistry
Mass Spectrometry
Oligopeptides / chemistry
Grant Support
Reg. No./Substance:
0/Carbodiimides; 0/Carboxylic Acids; 0/Dendrimers; 0/Gases; 0/Ions; 0/Oligopeptides; 9G34HU7RV0/Edetic Acid

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