Phospholipids chiral at phosphorus. Dramatic effects of phosphorus chirality on the deuterium NMR properties of the choline head group of phospholipids in the liquid crystalline phase

Journal Article · Sat Dec 01 00:00:00 EST 1990 · Biochemistry; (USA)

DOI:https://doi.org/10.1021/bi00501a008· OSTI ID:5527337

Loffredo, W M; Jiang, Rutai; Tsai, Mingdaw ^[1]

---

1. The Ohio State Univ., Columbus (USA)

To probe the motional and conformational propertis of the choline head group of 1,2-dipalmitoyl-sn-glycero-3-thiophosphocholine (DPPsC), the R{sub p}, S{sub p}, and R{sub p} {plus} S{sub p} isomers of ({alpha}-D{sub 2})DPPsC, ({beta}-D{sub 2})DPPsC, and ({delta}-D{sub 9})DPPsC in the subgel, gel, and liquid crystalline phases were investigated with deuterium NMR, and the results were compared with those of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) labeled at the same positions. In the subgel phase (5 {degree}C) all isomers of ({alpha}-D{sub 2})DPPsC and ({beta}-D{sub 2})DPPsC displayed amorphous line shapes characteristic of a restricted and disordered motional environment, whereas ({delta}-D{sub 9})DPPsC showed narrower and symmetric line shapes indicating substantial motions. For all three labeled positions the apparent line width of the R{sub p} isomer is larger than those of S{sub p} and R{sub p} {plus} S{sub p} isomers, and the amorphous line shape of the R{sub p} isomer also persists at 25 and 35{degree}C. These results indicate that the motional and conformational properties of the C{sub {alpha}}-C{sub {beta}} segment of DPPsC is very sensitive to the configuration at phosphorus. Structurally, this provides strong support for noncovalent interactions between the quaternary ammonium group of choline and the phosphate group of a neighboring molecule in the bilayers of phosphatidylcholine and suggests that such interactions are important to the motion of the choline chain.

• OSTI ID: 5527337
• Journal Information: Biochemistry; (USA), Vol. 29:49; ISSN 0006-2960
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
CHOLINE
CONFORMATIONAL CHANGES
PHOSPHOLIPIDS
NUCLEAR MAGNETIC RESONANCE
PHOSPHORUS COMPOUNDS
CHIRALITY
DEUTERIUM COMPOUNDS
ISOMER SHIFT
NMR SPECTRA
PHASE STUDIES
ALCOHOLS
AMINES
AMMONIUM COMPOUNDS
DRUGS
ESTERS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
LIPIDS
LIPOTROPIC FACTORS
MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PARTICLE PROPERTIES
QUATERNARY COMPOUNDS
RESONANCE
SPECTRA
550201* - Biochemistry- Tracer Techniques