PMID- 38517348
OWN - NLM
STAT- MEDLINE
DCOM- 20240408
LR  - 20240408
IS  - 1523-7052 (Electronic)
IS  - 1523-7060 (Print)
IS  - 1523-7052 (Linking)
VI  - 26
IP  - 13
DP  - 2024 Apr 5
TI  - Peptide and Protein Desulfurization with Diboron Reagents.
PG  - 2590-2595
LID - 10.1021/acs.orglett.4c00609 [doi]
AB  - In this Letter, we report a direct and robust desulfurization method employing 
      water-soluble phosphine, specifically tris(2-carboxyethyl)phosphine hydrochloride 
      (TCEP), and tetrahydroxydiboron (B(2)(OH)(4)), which serves as a radical 
      initiator. This innovative reaction exhibits compatibility with a diverse array 
      of substrates, including cysteine residues in chemically synthesized 
      oligopeptides and cyclic peptides, alkyl thiols in bioactive molecules, 
      disulfides in commercial proteins, and selenocysteine. We optimized the reaction 
      conditions to minimize the formation of undesired oxidized and borylated 
      byproducts. Furthermore, the refined desulfurization process is executed after 
      native chemical ligation (NCL) in a single pot, streamlining the existing 
      synthetic approaches. This demonstrates its potential applications in the 
      synthesis of complex peptides and proteins, showcasing a significant advancement 
      in the field.
FAU - Jing, Ruiheng
AU  - Jing R
AD  - Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United 
      States.
FAU - Walczak, Maciej A
AU  - Walczak MA
AUID- ORCID: 0000-0002-8049-0817
AD  - Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United 
      States.
LA  - eng
GR  - R01 GM138682/GM/NIGMS NIH HHS/United States
PT  - Journal Article
DEP - 20240322
PL  - United States
TA  - Org Lett
JT  - Organic letters
JID - 100890393
RN  - 0 (Indicators and Reagents)
RN  - 0 (Peptides)
RN  - 0 (Proteins)
RN  - K848JZ4886 (Cysteine)
RN  - 0 (Sulfhydryl Compounds)
SB  - IM
MH  - Indicators and Reagents
MH  - *Peptides/chemistry
MH  - *Proteins/chemistry
MH  - Cysteine/chemistry
MH  - Sulfhydryl Compounds/chemistry
PMC - PMC10999128
MID - NIHMS1979901
COIS- The authors declare no competing financial interest.
EDAT- 2024/03/22 12:46
MHDA- 2024/04/08 06:42
PMCR- 2024/04/07
CRDT- 2024/03/22 10:44
PHST- 2024/04/08 06:42 [medline]
PHST- 2024/03/22 12:46 [pubmed]
PHST- 2024/03/22 10:44 [entrez]
PHST- 2024/04/07 00:00 [pmc-release]
AID - 10.1021/acs.orglett.4c00609 [doi]
PST - ppublish
SO  - Org Lett. 2024 Apr 5;26(13):2590-2595. doi: 10.1021/acs.orglett.4c00609. Epub 
      2024 Mar 22.