Structure of a novel phosphocholine-containing glycoglycerolipid from Mycoplasma fermentans.
Mycoplasma fermentans is thought to be a pathogen of rheumatoid arthritis or cofactor of AIDS. A novel phosphocholine-containing glycoglycerophospholipid named GGPL-I was isolated from a M. fermentans-infected human helper T-cell culture. It was revealed that GGPL-I is a lipid component of the M. fermentans and a major immunological determinant. The GGPL-I was purified by DEAE-Sephadex column chromatography and repeated Iatrobeads column chromatography. The purified glycophospholipid was subjected to structural characterization by thin-layer chromatography, Fourier-transform infrared spectrometry, liquid secondary ion mass spectrometry, and nuclear magnetic resonance spectroscopy. Its structure was determined to be as follows: 6'-O-phosphocholine-alpha-glucopyranosyl-(1'-3)-1,2-diacyl-sn-glycerol. This glycoglycerophospholipid is unique in containing phosphocholine, which is attached to C-6 of glucose. The stereospecific numbering (sn) of naturally occurring GGPL-I was determined through comparison with chemically synthesized compounds.
Matsuda
K
K
Department of Microbiology, Faculty of Medicine, Tokyo Medical and Dental University, Japan.
Kasama
T
T
Ishizuka
I
I
Handa
S
S
Yamamoto
N
N
Taki
T
T
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002460:Cell Line; D002794:Choline / Q000032:analysis; D005947:Glucose / Q000032:analysis; D005990:Glycerol / Q000032:analysis; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D016858:Mycoplasma fermentans / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D006377:T-Lymphocytes, Helper-Inducer / Q000382:microbiology
D006017:Glycolipids; C091226:6'-O-phosphocholineglucopyranosyl-(1'-3)-1,2-dipalmitoyl; D005947:Glucose; D002794:Choline; D005990:Glycerol