1H NMR studies of a biosynthetic lacto-ganglio hybrid glycosphingolipid: confirmation of structure, interpretation of "anomalous" chemical shifts, and evidence for interresidue amide-amide hydrogen bonding.
1H NMR studies of a biosynthetic lacto-ganglio hybrid glycosphingolipid: confirmation of structure, interpretation of "anomalous" chemical shifts, and evidence for interresidue amide-amide hydrogen bonding.
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生物合成乳神经节杂合鞘糖脂的 1H NMR 研究：结构确认、“异常”化学位移的解释以及残基间酰胺-酰胺氢键的证据。
DOI：
10.1021/bi00119a016
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发表时间：
1992
期刊：
影响因子：
2.9
通讯作者：
Hakomori,S
中科院分区：
文献类型：
--
作者：
Levery,SB;Holmes,EH;Harris,DD;Hakomori,S
Steven B. Levery,** 4 Eric H. Holmes, § Dwayne D. Harris, 1* and Sen-itiroh Hakomori1 The Biomembrane Institute and University of Washington, 201 Elliott Avenue West, Seattle, Washington 98119, and Pacific Northwest Research Foundation, 720 Broadway, Seattle, Washington 98122 Received May 16, 1991; Revised Manuscript Received October 21, 1991 abstract: Glycosphingolipids bearing GlcNAc/31—*-3 and GalNAc/31—* 4linked to/3-Gal of lactosylceramide (lacto-ganglio hybrids), first isolated from a murine myelogenous leukemia cell line [Kannagi, R., Levery, S. B., & Hakomori, S.(1984) J. Biol. Chem. 259, 8444-8451], have since been found as normal components of mullet roe and English sole liver. In order to clarify the biosynthetic pathways responsible for its occurrence both as a product of normal tissues and as a possible mammalian cancer-associated antigen, the lacto-ganglio hybrid core structure LcGg4Cer was synthesized from Lc3Cer using a GalNAc/31—> 4 transferase preparation from English sole liver. A preliminary characterization of the enzyme, which may be identical to the GalNAc Tl responsible for synthesis of GM2 ganglioside, is presented. The enzymatically synthesized product was analyzed by 1-and 2-D'H NMR spectroscopy, confirming its primary structure as GalNAc/31—* 4-(GlcNAc/31—»-3) Gal/31—» 4Glc/31-»-lCer. In addition to assigning all nonexchangeable glycosyl proton resonances, measurements of several properties of the amide NH protons, including chemical shift, coupling constants, exchange rates, and temperatureshift coefficients, were obtained and compared to those in the simpler constituent triglycosylceramides, Lc3-and Gg3Cer. An approximate three-dimensional structure for LcGg4Cer is proposed, consistent with all data obtained, which should be useful in discussing the results of’Hnmr analysis of compounds containing this core tetrasaccharide. The structure is characterized by an unusual arrangement of terminal TV-acetylhexosamine residues, resulting in a xH hydrogen-bonding interaction between their acetamido groups.(jTlycosphingolipids bearing GlcNAc/31-*-3 and GalNAc/31—* 4 linked to/3-Gal of lactosylceramide (see Figure 1) are hybrids of the lacto-and ganglio series (neo-lactoganglio when extended by Gal/Sl—> 4 to/S-GlcNAc). First isolated from a murine myelogenous leukemia cell line (Ml) in its undifferentiated form (Kannagi et al., 1983, 1984), glycosphingolipids of this type were subsequently found in mullet roe (DeGasperi et al., 1987) and in the liver of English sole (Ostrander et al., 1988a)(see Table I). Lacto-gangliotetraosylceramide (LcGg4Cer)'has been synthesized both chemically (Shigeta et al., 1987) and enzymatically, using lactotriaosylceramide (Lc3Cer) and a/S-GalNAc transferase from guinea pig bone marrow(Das et al., 1987a). It is thus possible that, once the enzymatic pathways governing its biosynthesis are clarified, and the signs of its presence become more familiar to analytical biochemists using modern techniques such as high-resolution NMR, this glycosphingolipid core structure, which was at first considered a novelty confined to a unique in vitro murine system, may be found to be dis-tributed in a wider variety of normal (and abnormal) tissues. We report the results of studies in both of these areas (biosynthesis and NMR), which are closely related in that both are considerably illuminated by an appreciation of three-di-fThis study was supported by funds from National Institutes of Health Outstanding Investigator Grant CA42505 (to SH), National Institute of Environmental Health Sciences/NIH Research Grant ES04370 (to EHH), and fundsfrom The …
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培养仓鼠（无）细胞中鞘糖脂 β-N-乙酰半乳糖胺基转移酶活性的表征。
DOI：
10.1016/0005-2760(82)90339-3
发表时间：
1982
期刊：
Biochimica et biophysica acta
影响因子：
--
作者：
Lockney,MW;Sweeley,CC
通讯作者：
Sweeley,CC
马铁细胞色素 c 中的瞬时质子-质子奥弗豪瑟效应
影响因子：
15
作者：
S. Gordon;K. Wuethrich
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K. Wuethrich
具有杂合新乳神经节型糖链的神经节苷脂的分离和表征。
DOI：
--
发表时间：
1987
期刊：
The Journal of biological chemistry
影响因子：
--
作者：
DeGasperi,R;Koerner,TA;Quarles,RH;Ilyas,AA;Ishikawa,Y;Li,SC;Li,YT
通讯作者：
Li,YT
影响因子：
4.8
作者：
J. Steigerwald;S. Basu;B. Kaufman;S. Roseman
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S. Roseman
大鼠肝脏中神经节苷脂的生物合成。
DOI：
--
发表时间：
1981
期刊：
European Journal of Biochemistry
影响因子：
--
作者：
H. Senn;C. Cooper;P. Warnke;M. Wagner;K. Decker
通讯作者：
K. Decker