Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology
Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis rou...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/7/2199 |
| _version_ | 1797438396797288448 |
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| author | Zachary J. Struzik Shruti Biyani Tim Grotzer Judith Storch David H. Thompson |
| author_facet | Zachary J. Struzik Shruti Biyani Tim Grotzer Judith Storch David H. Thompson |
| author_sort | Zachary J. Struzik |
| collection | DOAJ |
| description | Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis route utilized phosphoramidite methodology that addressed issues surrounding fatty acid substrate scope and glycerol backbone modifications prior to headgroup phosphorylation, but faltered in the reproducibility of the overall pathway due to purification challenges. Herein, we present a robust pathway to optically pure PG in fewer steps, utilizing H-phosphonates that features a chromatographically friendly and stable triethyl ammonium H-phosphonate salt. Our route is also amendable to the simultaneous installation of different acyl chains, either saturated or unsaturated, on the glycerol backbone. |
| first_indexed | 2024-03-09T11:37:19Z |
| format | Article |
| id | doaj.art-95909754627540bd886d9bedf2f96647 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:37:19Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-95909754627540bd886d9bedf2f966472023-11-30T23:40:56ZengMDPI AGMolecules1420-30492022-03-01277219910.3390/molecules27072199Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate MethodologyZachary J. Struzik0Shruti Biyani1Tim Grotzer2Judith Storch3David H. Thompson4Bindley Bioscience Center, Department of Chemistry, Multi-Disciplinary Cancer Research Facility, Purdue University, 1203 W. State Street, West Lafayette, IN 47907, USABindley Bioscience Center, Department of Chemistry, Multi-Disciplinary Cancer Research Facility, Purdue University, 1203 W. State Street, West Lafayette, IN 47907, USABindley Bioscience Center, Department of Chemistry, Multi-Disciplinary Cancer Research Facility, Purdue University, 1203 W. State Street, West Lafayette, IN 47907, USADepartment of Nutritional Sciences and Rutgers Center for Lipid Research, Rutgers University, New Brunswick, NJ 08901, USABindley Bioscience Center, Department of Chemistry, Multi-Disciplinary Cancer Research Facility, Purdue University, 1203 W. State Street, West Lafayette, IN 47907, USANaturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis route utilized phosphoramidite methodology that addressed issues surrounding fatty acid substrate scope and glycerol backbone modifications prior to headgroup phosphorylation, but faltered in the reproducibility of the overall pathway due to purification challenges. Herein, we present a robust pathway to optically pure PG in fewer steps, utilizing H-phosphonates that features a chromatographically friendly and stable triethyl ammonium H-phosphonate salt. Our route is also amendable to the simultaneous installation of different acyl chains, either saturated or unsaturated, on the glycerol backbone.https://www.mdpi.com/1420-3049/27/7/2199phospholipid synthesisphosphatidyl glycerolH-phosphonatesphosphoramidites |
| spellingShingle | Zachary J. Struzik Shruti Biyani Tim Grotzer Judith Storch David H. Thompson Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology Molecules phospholipid synthesis phosphatidyl glycerol H-phosphonates phosphoramidites |
| title | Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology |
| title_full | Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology |
| title_fullStr | Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology |
| title_full_unstemmed | Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology |
| title_short | Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology |
| title_sort | synthesis of phosphatidyl glycerol containing unsymmetric acyl chains using h phosphonate methodology |
| topic | phospholipid synthesis phosphatidyl glycerol H-phosphonates phosphoramidites |
| url | https://www.mdpi.com/1420-3049/27/7/2199 |
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