Journal article
Proline-based phosphoramidite reagents for the reductive ligation of S-nitrosothiols
Journal of antibiotics, Vol.69(4), pp.313-318
04/2016
Handle:
https://hdl.handle.net/2376/114534
PMCID: PMC4848125
PMID: 26758493
Abstract
S-Nitrosothiols (RSNOs) have many biological implications but are rarely used in organic synthesis. In this work we report the development of proline-based phosphoramidite substrates that can effectively convert RSNOs to proline-based sulfenamides through a reductive ligation process. A unique property of this method is that the phosphine oxide moiety on the ligation products can be readily removed under acidic conditions. In conjugation with the facile preparation of RSNOs from the corresponding thiols (RSHs), this method provides a new way to prepare proline-based sulfenamides from simple thiol starting materials.
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Details
- Title
- Proline-based phosphoramidite reagents for the reductive ligation of S-nitrosothiols
- Creators
- Chung-Min Park - Department of Chemistry, Washington State University, Pullman, WA 99164, United StatesTyler D Biggs - Department of Chemistry, Washington State University, Pullman, WA 99164, United StatesMing Xian - Department of Chemistry, Washington State University, Pullman, WA 99164, United States
- Publication Details
- Journal of antibiotics, Vol.69(4), pp.313-318
- Academic Unit
- Chemistry, Department of
- Publisher
- Japan
- Grant note
- R01 GM088226 / NIGMS NIH HHS
- Identifiers
- 99900548291001842
- Language
- English
- Resource Type
- Journal article