Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine. / Papangelis, Nassos; Ulven, Trond.

In: The Journal of Organic Chemistry, Vol. 87, No. 12, 2022, p. 8194–8197.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Papangelis, N & Ulven, T 2022, 'Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine', The Journal of Organic Chemistry, vol. 87, no. 12, pp. 8194–8197. https://doi.org/10.1021/acs.joc.2c00335

APA

Papangelis, N., & Ulven, T. (2022). Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine. The Journal of Organic Chemistry, 87(12), 8194–8197. https://doi.org/10.1021/acs.joc.2c00335

Vancouver

Papangelis N, Ulven T. Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine. The Journal of Organic Chemistry. 2022;87(12):8194–8197. https://doi.org/10.1021/acs.joc.2c00335

Author

Papangelis, Nassos ; Ulven, Trond. / Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine. In: The Journal of Organic Chemistry. 2022 ; Vol. 87, No. 12. pp. 8194–8197.

Bibtex

@article{d743599b089c46259ee9c98f17b7e2da,
title = "Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine",
abstract = "Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without chromatography by an exceedingly mild TBS deprotection, using 1 equiv of TFA in aqueous solution. The method enabled the synthesis of glycerol-, acyl-, and choline-labeled LPC.",
author = "Nassos Papangelis and Trond Ulven",
year = "2022",
doi = "10.1021/acs.joc.2c00335",
language = "English",
volume = "87",
pages = "8194–8197",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "12",

}

RIS

TY - JOUR

T1 - Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine

AU - Papangelis, Nassos

AU - Ulven, Trond

PY - 2022

Y1 - 2022

N2 - Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without chromatography by an exceedingly mild TBS deprotection, using 1 equiv of TFA in aqueous solution. The method enabled the synthesis of glycerol-, acyl-, and choline-labeled LPC.

AB - Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without chromatography by an exceedingly mild TBS deprotection, using 1 equiv of TFA in aqueous solution. The method enabled the synthesis of glycerol-, acyl-, and choline-labeled LPC.

U2 - 10.1021/acs.joc.2c00335

DO - 10.1021/acs.joc.2c00335

M3 - Journal article

C2 - 35649118

VL - 87

SP - 8194

EP - 8197

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 12

ER -

ID: 311457455