PMID- 35763672
OWN - NLM
STAT- MEDLINE
DCOM- 20220718
LR  - 20220919
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 87
IP  - 14
DP  - 2022 Jul 15
TI  - Thiol Catalysis of Selenosulfide Bond Cleavage by a Triarylphosphine.
PG  - 9426-9430
LID - 10.1021/acs.joc.2c00934 [doi]
AB  - The arylthiol 4-mercaptophenylacetic acid (MPAA) is a powerful catalyst of 
      selenosulfide bond reduction by the triarylphosphine 
      3,3',3''-phosphanetriyltris(benzenesulfonic acid) trisodium salt (TPPTS). Both 
      reagents are water-soluble at neutral pH and are particularly adapted for working 
      with unprotected peptidic substrates. Contrary to trialkylphosphines such as 
      tris(2-carboxyethyl)phosphine hydrochloride (TCEP), TPPTS has the advantage of 
      not inducing deselenization reactions. We believe that the work reported here 
      will be of value for those manipulating selenosulfide bonds in peptidic or 
      protein molecules.
FAU - Firstova, Olga
AU  - Firstova O
AD  - Univ. Lille, CNRS, INSERM, CHU Lille, Institut Pasteur de Lille, U1019 - UMR 9017 
      - CIIL - Center for Infection and Immunity of Lille, F-59000 Lille, France.
FAU - Melnyk, Oleg
AU  - Melnyk O
AUID- ORCID: 0000-0002-3863-5613
AD  - Univ. Lille, CNRS, INSERM, CHU Lille, Institut Pasteur de Lille, U1019 - UMR 9017 
      - CIIL - Center for Infection and Immunity of Lille, F-59000 Lille, France.
FAU - Diemer, Vincent
AU  - Diemer V
AD  - Univ. Lille, CNRS, INSERM, CHU Lille, Institut Pasteur de Lille, U1019 - UMR 9017 
      - CIIL - Center for Infection and Immunity of Lille, F-59000 Lille, France.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20220628
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
RN  - 0 (Indicators and Reagents)
RN  - 0 (Peptides)
RN  - 0 (Phosphines)
RN  - 0 (Proteins)
RN  - 0 (Sulfhydryl Compounds)
SB  - IM
MH  - Catalysis
MH  - Indicators and Reagents
MH  - Peptides/chemistry
MH  - *Phosphines/chemistry
MH  - Proteins/chemistry
MH  - *Sulfhydryl Compounds
EDAT- 2022/06/29 06:00
MHDA- 2022/07/19 06:00
CRDT- 2022/06/28 15:22
PHST- 2022/06/29 06:00 [pubmed]
PHST- 2022/07/19 06:00 [medline]
PHST- 2022/06/28 15:22 [entrez]
AID - 10.1021/acs.joc.2c00934 [doi]
PST - ppublish
SO  - J Org Chem. 2022 Jul 15;87(14):9426-9430. doi: 10.1021/acs.joc.2c00934. Epub 2022 
      Jun 28.