A synthesis of phospholipids using a phosphite-triester approach and uniformly cleavable β-halogenated protecting groups

Peter Lemmen; Karin M. Buchweitz; Renate Stumpf

doi:10.1016/0009-3084(90)90134-D

A synthesis of phospholipids using a phosphite-triester approach and uniformly cleavable β-halogenated protecting groups

Peter Lemmen
, Karin M. Buchweitz
, Renate Stumpf

Natural Sciences

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

A new method for the synthesis of phospholipids is described. It is characterized by the use of a phosphite-amide-triester strategy, adopted from oligonucleotide chemistry, and by the use of protective groups which are cleavable by reductive fragmentation. Phosphorous acid-1,1,1-trichloro-2-methyl-2-propylester- (TCB) chloride-dimethylamide is used as the phosphorylating agent. Thus TCB is used for the protection of phosphodiesters. Nitrogenfunctions are protected by the 1,1,1-trichloro-2-methyl-2-propyl-oxycarbonyl group (TCBOC) and 2-bromoethanole is used for the protection of carboxyl groups. The versatility of this method is demonstrated by the syntheses of 1,2-dimiristoyl-sn-glycero-3-phosphatidyl-ethanolamine (DMPE) and 1,2-dimyristoyl-sn-glycero-3-phosphatidyl-serine (DMPS).

Original language	English
Pages (from-to)	65-75
Number of pages	11
Journal	Chemistry and Physics of Lipids
Volume	53
Issue number	1
DOIs	https://doi.org/10.1016/0009-3084(90)90134-D
State	Published - Mar 1990

Keywords

DMPE
DMPS
phosphite treister
phospholipid synthesis
reductive fragmentation

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10.1016/0009-3084(90)90134-D

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@article{520afd94b48d4d7eaac38a481810110f,

title = "A synthesis of phospholipids using a phosphite-triester approach and uniformly cleavable β-halogenated protecting groups",

abstract = "A new method for the synthesis of phospholipids is described. It is characterized by the use of a phosphite-amide-triester strategy, adopted from oligonucleotide chemistry, and by the use of protective groups which are cleavable by reductive fragmentation. Phosphorous acid-1,1,1-trichloro-2-methyl-2-propylester- (TCB) chloride-dimethylamide is used as the phosphorylating agent. Thus TCB is used for the protection of phosphodiesters. Nitrogenfunctions are protected by the 1,1,1-trichloro-2-methyl-2-propyl-oxycarbonyl group (TCBOC) and 2-bromoethanole is used for the protection of carboxyl groups. The versatility of this method is demonstrated by the syntheses of 1,2-dimiristoyl-sn-glycero-3-phosphatidyl-ethanolamine (DMPE) and 1,2-dimyristoyl-sn-glycero-3-phosphatidyl-serine (DMPS).",

keywords = "DMPE, DMPS, phosphite treister, phospholipid synthesis, reductive fragmentation",

author = "Peter Lemmen and Buchweitz, \{Karin M.\} and Renate Stumpf",

note = "Funding Information: We are indebted to Mrs. M. Koenig for expert technical assistance and to Mr. T. Bayerl for measuring the DSC. Financial support of this work by the Deutsche Forschungsgemeinschaft is gratefully acknowledged.",

year = "1990",

month = mar,

doi = "10.1016/0009-3084(90)90134-D",

language = "English",

volume = "53",

pages = "65--75",

journal = "Chemistry and Physics of Lipids",

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T1 - A synthesis of phospholipids using a phosphite-triester approach and uniformly cleavable β-halogenated protecting groups

AU - Lemmen, Peter

AU - Buchweitz, Karin M.

AU - Stumpf, Renate

N1 - Funding Information: We are indebted to Mrs. M. Koenig for expert technical assistance and to Mr. T. Bayerl for measuring the DSC. Financial support of this work by the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

PY - 1990/3

Y1 - 1990/3

N2 - A new method for the synthesis of phospholipids is described. It is characterized by the use of a phosphite-amide-triester strategy, adopted from oligonucleotide chemistry, and by the use of protective groups which are cleavable by reductive fragmentation. Phosphorous acid-1,1,1-trichloro-2-methyl-2-propylester- (TCB) chloride-dimethylamide is used as the phosphorylating agent. Thus TCB is used for the protection of phosphodiesters. Nitrogenfunctions are protected by the 1,1,1-trichloro-2-methyl-2-propyl-oxycarbonyl group (TCBOC) and 2-bromoethanole is used for the protection of carboxyl groups. The versatility of this method is demonstrated by the syntheses of 1,2-dimiristoyl-sn-glycero-3-phosphatidyl-ethanolamine (DMPE) and 1,2-dimyristoyl-sn-glycero-3-phosphatidyl-serine (DMPS).

AB - A new method for the synthesis of phospholipids is described. It is characterized by the use of a phosphite-amide-triester strategy, adopted from oligonucleotide chemistry, and by the use of protective groups which are cleavable by reductive fragmentation. Phosphorous acid-1,1,1-trichloro-2-methyl-2-propylester- (TCB) chloride-dimethylamide is used as the phosphorylating agent. Thus TCB is used for the protection of phosphodiesters. Nitrogenfunctions are protected by the 1,1,1-trichloro-2-methyl-2-propyl-oxycarbonyl group (TCBOC) and 2-bromoethanole is used for the protection of carboxyl groups. The versatility of this method is demonstrated by the syntheses of 1,2-dimiristoyl-sn-glycero-3-phosphatidyl-ethanolamine (DMPE) and 1,2-dimyristoyl-sn-glycero-3-phosphatidyl-serine (DMPS).

KW - DMPE

KW - DMPS

KW - phosphite treister

KW - phospholipid synthesis

KW - reductive fragmentation

UR - https://www.scopus.com/pages/publications/0025357591

U2 - 10.1016/0009-3084(90)90134-D

DO - 10.1016/0009-3084(90)90134-D

M3 - Article

AN - SCOPUS:0025357591

SN - 0009-3084

VL - 53

SP - 65

EP - 75

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 1

ER -

A synthesis of phospholipids using a phosphite-triester approach and uniformly cleavable β-halogenated protecting groups

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Keywords

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