| Gas-Phase Reactivity of Carboxylic Acid Functional Groups with Carbodiimides. | |
| | |
MedLine Citation:
|
PMID: 23208744 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
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. |
| | |
Authors:
|
Boone M Prentice; Joshua D Gilbert; John R Stutzman; William P Forrest; Scott A McLuckey |
Related Documents
:
|
18048014 - Ft-ir spectra of alginic acid block fractions in three species of brown seaweeds. 23150634 - Metabolic interactions between the lands cycle and the kennedy pathway of glycerolipid ... 10348044 - New types of liposidomycins produced by streptomyces that inhibit bacterial peptidoglyc... 23707484 - Fumaric acid attenuates the eotaxin-1 expression in tnf-α-stimulated fibroblasts by su... 15084584 - A c-terminal region dictates the apical plasma membrane targeting of the human sodium-d... 2669974 - Stimulus-secretion coupling of arginine-induced insulin release. metabolism of l-argini... |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2012-12-4 |
Journal Detail:
|
Title: Journal of the American Society for Mass Spectrometry Volume: - ISSN: 1879-1123 ISO Abbreviation: J. Am. Soc. Mass Spectrom. Publication Date: 2012 Dec |
Date Detail:
|
Created Date: 2012-12-4 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 9010412 Medline TA: J Am Soc Mass Spectrom Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
|
Department of Chemistry, Purdue University, West Lafayette, IN, 47907-2084, USA. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Infrared Matrix-Assisted Laser Desorption Electrospray Ionization (IR-MALDESI) Imaging Source Couple...
Next Document: Complete Mapping of a Cystine Knot and Nested Disulfides of Recombinant Human Arylsulfatase A by Mul...