The unexpected racemization and hydrogen–deuterium exchange of the hydrogen at the α-carbon of proline analogs containing the 5-azoniaspiro[4.4]nonyl-group‡
Literature Information
B. Setner, M. Wierzbicka, L. Jerzykiewicz, M. Lisowski, Z. Szewczuk
Recently, we developed a novel non-fragmenting quaternary ammonium ionization tag for the mass spectrometric sensitive sequencing of peptides, based on the N-spiro proline residue (5-azoniaspiro[4.4.]nonyl-carbonyl). Herein, we present an unexpected racemization and the hydrogen–deuterium exchange (HDX) at the α-C atom of the proline derivative under basic aqueous conditions (1% water solution of triethylamine). The deuterium atom, substituted for the α-C atom, does not undergo back-exchange under acidic aqueous conditions which makes the deuterated isotopologue a promising stabile isotope-coded internal standard for quantitative analysis by mass spectrometry. The applicability of the prepared isotopologues of the quaternary ammonium salt labeled peptides for quantification experiments using the isotopic dilution method was also examined.
Related Literature
Thermoresponsive hybrid double-crosslinked networks using magnetic iron oxide nanoparticles as crossing points
Thomas Blin, Antoine Niederberger, Lazhar Benyahia, Jérôme Fresnais, Véronique Montembault, Laurent Fontaine
DOI: 10.1039/C8PY01006D
Elastomeric and pH-responsive hydrogels based on direct crosslinking of the poly(glycerol sebacate) pre-polymer and gelatin
Biqiong Chen
DOI: 10.1039/C8PY00544C
Renewable polyols for advanced polyurethane foams from diverse biomass resources
Pierre Furtwengler, Luc Avérous
DOI: 10.1039/C8PY00827B
The effects of polymer topology and chain length on the antimicrobial activity and hemocompatibility of amphiphilic ternary copolymers
Rashin Namivandi-Zangeneh, Rebecca J. Kwan, Thuy-Khanh Nguyen, Jonathan Yeow, Frances L. Byrne, Edgar H. H. Wong, Cyrille Boyer
DOI: 10.1039/C7PY01069A
Polyallene-based amphiphilic triblock copolymer via successive free radical polymerization and ATRP
Hao Guo, Xiaoyu Huang
DOI: 10.1039/C7PY01407D
Effective macrophage delivery using RAFT copolymer derived nanoparticles
R. W. M. Davidson, G. W. Simpson, J. Chiefari, M. J. Fuchter
DOI: 10.1039/C7PY01363A
You might also like
What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?
(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...
What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?
5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...
What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?
Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...
Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?
1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...
What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?
[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...
What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?
6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...
What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?
This compound is primarily used in the pharmaceutical industry for the developme...
What are the main uses of 1-Ethyl-7-[2-methyl-6-(4H-1,2,4-triazol-3-yl)-3-pyridinyl]-3,5-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (CAS: 1228013-15-7)?
1-Ethyl-7-[2-methyl-6-(4H-1,2,4-triazol-3-yl)-3-pyridinyl]-3,5-dihydropyrazino[2...
Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?
Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...
What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?
3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.












![7-Bromo-5-chloro-1H-pyrazolo[4,3-b]pyridine structure 7-Bromo-5-chloro-1H-pyrazolo[4,3-b]pyridine structure](https://static.chemtradehub.com/structs/135/1351813-70-1-a716.webp)

