Other sphingoid bases & fatty acids N-Glycoloyl- Neu (NeuGc)* 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 Prepared by Meeyoung Park, Anu Koppikar, Akemi Suzuki, Alfred H. Merrill, Jr., Hyejung Park and the Sphingolipid Research Lab (http://sphingolab.biology.gatech.edu), School of Biology & Petit Institute for Bioengineering and Biosciences, Georgia Institute of Technology in affiliation with the Lipid Maps Consortium & the UGA Complex Carbohydrate Research Center. Acknowledgements We thank the following for suggestions: Eoin Fahy, Tony Futerman, Kentaro Hanada, Sen-itiroh Hakomori, Yoshio Hirabayashi, Jin-Young Hong, Michael “Hawkeye” Pierce, Konrad Sandhoff, Ronald L. Schnaar, Walt Shaw (Avanti Polar Lipids), M. Cameron Sullards, C. C. Sweeley, Elaine Wang and May Dongmei Wang And the following for support: the Lipid MAPS Consortium (GM69338, GM067877, Ed Dennis, PI), the Smithgall Institute Endowment for Molecular Cell Biology and the Petit Institute for Bioengineering & Bioscience at Georgia Tech, and the UGA Integrated Technology Resource for Biomedical Glycomics (PA-02-132, Michael Pierce, PI). βCer β4 253 β3 α3 sialyparagloboside βCer β4 42 β3 α3 N S E W nLc4Cer βCer β4 12 β3 nLc5Cer βCer β4 52 β3 nLc6Cer/i antigen βCer β4 53 β3 Type II H antigen βCer β4 54 β3 α2 Type II A antigen βCer β4 58 β3 α2 α3 βCer β4 SSEA-1, Lex 39 β3 α3 βCer β4 199 β3 βCer β4 200 β3 α3 A A βCer β4 268 β3 α3 βCer β4 362 β3 HSO3-6 βCer β4 44 β3 α3 α8 βCer β4 Lex-5 270 β3 α3 Type II B antigen βCer β4 56 β3 α2 α3 65 βCer β4 279 β3 α4 βCer β4 201 β3 α3 α4 βCer β4 117 β3 α2 α3 α3 βCer β4 261 β3 βCer β4 216 β3 α3 α8 βCer β4 269 β3 α3 βCer β4 361 β3 HSO3-3GluUβ3 α3 βCer β4 262 β3 α4 βCer β4 352 β3 α3 B α3 βCer β4 sialyl Lex 41 β3 α3 βCer β4 280 β3 α4 α3 βCer β4 202 β3 α4 www.lipidmaps.org Ley βCer β4 119 β3 α2 α3 βCer β4 351 β3 α2 α3 B βCer β4 229 β3 α3 βCer β4 263 β3 βCer β4 391 β3 α6 βCer β4 218 β3 α3 βCer β4 281 β3 α3 α3 βCer β4 264 β3 β6 βCer β4 120 β3 α2 α3 βCer β4 118 β3 α2 α3 Sphingoid base biosynthesis SSEA-4 Antigen βCer β4 40 β3 α6 Globo-series βCer β4 389 β3 α3 C α3 βCer β4 266 β3 β6 βCer β4 65 β3 α3 C 254 270 The major sphingoid bases of mammalian sphingolipids are 18-carbon amino alkanes and alkenes derived from serine and palmitoyl-CoA, and are abbreviated by the number of hydroxyls (d for di-, t for tri-, etc.), the carbon chain length and number of bonds; for example: Sphing-4-enine (sphingoosine) = d18:1. In the scheme below, other sphingoid bases are designated d,tA:B to reflect variation in alkyl chain length (A) (such as d20:1 in brain ganglisides and d14:1 in insects), number of double bonds (B) (such as sphing-4,8-diene, d18:2, in plants) and number of hydroxyl groups (such as 4-hydroxysphinganine, phytosphingosine, 4t18:0, and 6-hydroxysphingosine, 6-t18:1, in skin). Other variations include sidechain methylation and the presence of triple bonds. βCer β4 248 β3 α6 β6 α3 βCer β4 360 β3 β6 222 α3 βCer β4 390 β3 βCer β4 63 β3 α6 βCer β4 222 β3 α6 α3 βCer β4 60 β3 α3 βCer β4 145 α4 α3 βCer β4 α4 α3 β3 146 βCer β4 62 β3 α3 dimeric Lex βCer β4 213 β3 α3 βCer β4 231 β3 α3 βCer β4 249 β3 α6 β6 α3 βCer β4 265 β3 β6 α2 βCer β4 143 α4 α3 βCer β4 α4 α3 β3 144 βCer β4 115 α4 β3 α3 α8 65 D sialyl Lex βCer β4 66 β3 α3 D L-serine O α3 βCer β4 64 β3 α3 βCer β4 220 β3 βCer β4 112 α4 α3 βCer β4 α4 α3 β3 134 βCer β4 113 α4 β3 α3 α6 βCer β4 214 β3 α3 βCer β4 363 β3 HSO3-3GluUβ3 + βCer β4 230 β3 α4 βCer β4 251 β3 α3 α8 Palmitoyl-CoA N or Stearoyl-CoA βCer β4 111 α4 α3 βCer β4 α4 α3 β3 133 α3 βCer β4 66 β3 sialyl Lex βCer β4 250 β3 α3 βCer β4 252 β3 α3 α8 βCer β4 125 β3 Phosphoethanolamine G or other fatty acyl-CoA’s βCer β4 SSEA-4 24 α4 β3 α3 sialyl dimeric Lex α3 βCer β4 221 β3 3-Ketosphinganine M βCer β4 215 β3 α3 E βCer β4 110 α4 α3 βCer β4 α4 α3 β3 132 E βCer β4 233 β3 βCer β4 283 β3 α3 βCer β4 256 β3 α3 βCer β4 124 β3 Sphingosine-1P F Sphinganine-1P H βCer β4 β3 α3 254 Sphinganine (d18:0) L α2 βCer β4 α4 α3 140 βCer β4 114 α4 β3 α3 α6 βCer β4 47 β3 α2 βCer β4 257 β3 α3 βCer β4 123 β3 α3 Lex 65 βCer β4 405 α4 β3 SO3H-3 Sphingosine (d18:1) D βCer β4 369 β3 α2 βCer β4 247 β3 α3 α3 βCer β4 288 β3 α8 4-Hydroxysphinganine K βCer β4 SSEA-4 positional isomer 406 α4 β3 α6 α3 βCer β4 137 α4 β3 βCer β4 43 β3 α3 F F βCer β4 258 β3 α3 βCer β4 122 β3 α3 dimeric Lex βCer β4 370 β3 α2 α3 α3 βCer β4 223 β3 β6 ?? α3 βCer β4 225 β3 β6 βCer β4 Gb3Cer, pk antigen α4 7 Dihydroceramides & other homologs βCer β4 Gb4Cer, P antigen 18 α4 β3 Gb5Cer, SSEA-3 β3 βCer β4 21 α4 Galα3 Ley βCer β4 388 β3 α3 βCer β4 409 β3 α2 α3 I βCer β4 259 β3 α3 d18:0; 16:0 d18:0; 20:0 d18:0; 24:1 d18:0; 26:1 d18:0; Cx:y α3 βCer β4 224 β3 β6 α3 βCer β4 226 β3 β6 βCer β4 20 α4 β3 βCer β4 typeIV H antigen 26 α4 β3 α2 βCer β4 121 β3 α3 trimeric Lex βCer β4 271 β3 α3 234 G d,tA:B; Cx:y G d18:0; 18:0 d18:0; 22:0 d18:0; 24:0 d18:0; 26:0 βCer β4 Forssman antigen 19 α4 β3 α3 Type II H antigen βCer β4 45 β3 α2 Type II B antigen βCer β4 46 β3 α2 α3 βCer β4 typeIV B antigen 28 α4 β3 α2 α3 βCer β4 272 β3 α3 α3 βCer β4 285 β3 β6 α2 α3 βCer β4 267 β3 β6 d18:1; 16:0 t18:0; 16:0 d18:1; 20:0 t18:0; 20:0 d18:1; 24:1 t18:0; 24:1 d18:1; 26:1 t18:0; 26:1 d18:1; Cx:y t18:0; Cx:y Other sphingoid bases & fatty acids βCer β4 Branched Forssman 139 α4 β3 α3 Type II A antigen βCer β4 386 β3 α2 α3 Ley βCer β4 48 β3 α2 α3 βCer β4 274 β3 α3 d18:1; 18:0 t18:0; 18:0 d18:1; 22:0 t18:0; 22:0 d18:1; 24:0 t18:0; 24:0 d18:1; 26:0 t18:0; 26:0 βCer β4 typeIV A antigen 27 α4 β3 α2 α3 βCer β4 286 β3 β6 α2 α3 ?3 α3 βCer β4 228 β3 β6 α2 βCer β4 273 β3 α3 H α3 βCer β4 203 β3 H Ceramides & 4-Hydroxydihydroceramides (Phytoceramides) Yeast Phytoceramide βCer β4 142 α4 β3 α3 α2 βCer β4 49 β3 α2 α3 1 J βCer β4 232 β3 α2 α3 βCer β4 135 α4 β3 α3 α3 βCer β4 241 β3 “Ceramides” are N-acyl-sphingoid bases. The fatty acids are designated by Cx:y to reflect chain length (x), double bonds (y), and other modifications (e.g. α-hydroxy, αh-, not shown). Other fatty acid variations include -hydroxylation (in skin). α3 βCer β4 205 β3 β6 βCer β4 287 β3 β6 α2 α3 βCer 2 GlcCer βCer β4 138 α4 β3 NeoLacto-series βCer β4 55 β3 β6 Glc-series βCer β4 136 α4 β3 α8 α3 Type III H antigen βCer β4 50 β3 α2 α3 α3 βCer β4 242 β3 β6 I I βCer 5 GalCer βCer β4 131 α4 β3 βCer β4 260 β3 α2 α3 βCer 13 GM4 α3 β6 β3 βCer β4 22 α4 α3 βCer β4 207 β3 β6 Gal-series Sialyl-paragloboside I antigen βCer β4 57 β3 β6 βCer 6 β4 SO3H-3 β3 β3 α4 β4 βCer βCer β4 284 β3 β6 α2 Type III A antigen βCer β4 51 β3 α2 α3 α3 βCer β4 243 β3 β6 403 α6 βCer β4 212 β3 β6 Phospho-series SO3H-3 βCer βCer 9 Gala-series α4 βCer 10 β4 α3 Mollu-series βCer 14 β4 Arthro-series β4 β6 β3 βCer 23 α4 SM4s βCer β4 366 β3 β6 α2 J βCer β4 59 β3 β6 α2 J Ceramide phosphate Z 16 Not all members are shown Not all members are shown Not all members are shown α3 βCer β4 244 β3 β6 Nomenclature for classification of glycosphingolipids Root name Carbohydrate in the ‘root’ structure (Abbrev) IV III II I Ganglio (Gg) Lacto (Lc) Neolacto (nLc) Globo (Gb) Isoglobo (iGb) Mollu (Mu) Arthro (At) Galβ1–3GalNacβ1–4Galβ1–4Glcβ1-Cer Galβ1–3GlcNacβ1–3Galβ1–4Glcβ1-Cer Galβ1–4GlcNacβ1–3Galβ1–4Glcβ1-Cer GalNacβ1–3Galα1–4Galβ1–4Glcβ1-Cer GalNacβ1–3Galα1–3Galβ1–4Glcβ1-Cer GalNacβ1–2Manα1–3Manβ1–4Glcβ1-Cer GalNacβ1–4GlcNacβ1–3Manβ1–4Glcβ1-Cer SphinGOMAP Symbol Key βCer β4 234 β3 β6 α3 βCer β4 25 α4 β3 β6 α3 Galactose Gal Glucose Glc Mannose Man Fucose Fuc Xylose Xyl Neuraminic Acid (Neu5Ac) N-Glycoloyl- Neu (NeuGc)* KDN* IdoA* Hexoses N-Acetylhexosamines Hexosamines Acidic Sugars Other Ceramide phosphocholine Cer-O-P(O2H)-O-CH2CH2N(CH3)3 Sphingomyelin A lyco ntologies etabolomics βCer 350 α4 SO3H-3 βCer β4 SM3 356 SO3H-3 βCer β4 364 β3 β6 α3 βCer β4 61 β3 β6 α2 α3 Sphingosyl-phosphocholine C α3 βCer β4 245 β3 β6 βCer β4 235 β3 β6 α3 K Sulfatides K P Ceramide phosphoethanolamine βCer β4 169 β3 α? Phytoceramide phosphoinositol(s) R Phytoceramide phosphoinositol- phosphates & other derivatives α3 βCer β4 246 β3 β6 βCer β4 236 β3 β6 α3 βCer β4 367 β3 β6 α2 α3 βCer β4 211 β3 SO3-6 α3 βCer β4 238 β3 β6 Phosphosphingolipids Documented Molecule* βCer … Documented Pathway* Molecule Number L βCer β4 247 β3 α3 βCer β4 407 β3 βCer β4 210 β3 2 L α3 βCer β4 237 β3 β6 Q Ceramide ciliatine 7/14/07 Version 1.4 Potential Intermediate βCer … Potential Pathway See notes below α3 βCer β4 β3 β6 240 Ganglioside GD2 βCer β4 368 β3 β6 α2 α3 (Phosphono-) Ganglioside GD1a α3 βCer β4 239 β3 β6 Ceramide arsenocholine B βCer β4 Lc3Cer 4 β3 (Arseno-) βCer β4 LacCer 3 βCer β4 iGb3 11 α3 M β4 βCer 377 α3 β4 βCer SMiGb4Cer 355 α3 SO3H-3 βCer β4 318 α3 M Placenta (biosynthesis unknown) β3 β4 β6 βCer 413 βCer β4 320 β3 α3 GD1a 9-O-Ac βCer β4 328 β3 α3 βCer β4 380 α3 α2 82 β3 βCer β4 iGb4, Cytolipin R 353 α3 Sialyl-Lea Ganglio-series βCer β4 317 α3 β4 βCer iGb5 354 α3 β3 β4 βCer SMiGb5Cer 412 α3 β3 HSO3-3 βCer β4 392 α3 βCer β4 411 α3 α2 Lacto-series βCer β4 316 β3 α3 βCer β4 315 β3 α3 KDN GD1a β3 βCer β4 378 α3 βCer β4 372 α3 β3 N β4 βCer 401 α3 β3 α6 N βCer β4 307 β3 α3 βCer β4 322 β3 α3 α6 GD1α2 β3 βCer β4 379 α3 βCer β4 Lc4Cer 8 β3 86 βCer β4 384 α3 βCer β4 30 β3 α3 βCer β4 208 β3 α6 βCer β4 151 β3 α3 IsoGlobo-series β3 βCer β4 382 α3 α2 βCer β4 308 β3 α3 GalNAc-GD1a β3 βCer β4 383 α3 α2 βCer β4 306 β3 α3 βCer β4 321 β3 α3 α6 GD1α2 βCer β4 385 α3 β3 βCer β4 163 β3 βCer β4 150 β3 α3 β3 βCer β4 381 α3 O βCer β4 ALeb 37 β3 α2 α3 α4 O βCer β4 340 α3 β3 GD1a βCer β4 164 β3 α3 βCer β4 152 β3 α3 βCer β4 319 β3 α3 GD1a βCer β4 300 β3 α3 βCer β4 341 β3 α3 βCer β4 195 β3 α3 α2 β6 βCer β4 sialyl Lea 32 β3 α3 α4 βCer β4 196 β3 α6 βCer β4 337 α3 β3 α2 βCer β4 393 α3 β3 βCer β4 395 α3 β3 βCer β4 Type I A antigen 35 β3 α2 α3 βCer β4 373 α3 β3 βCer β4 314 β3 α3 βCer β4 301 β3 α3 βCer β4 148 β3 α3 α4 β6 P P βCer β4 374 α3 β3 βCer β4 297 β3 α3 βCer β4 147 β3 α3 α4 β6 βCer β4 333 α3 β3 βCer β4 α3 β3 394 βCer β4 396 α3 β3 βCer β4 Leb 38 β3 α2 α4 βCer β4 194 β3 α3 α2 β6 βCer β4 Type I H antigen 33 β3 α2 βCer β4 402 α3 α8 Ac-9 βCer β4 375 α3 β3 βCer β4 298 β3 α3 βCer β4 299 β3 α3 368 βCer β4 149 β3 α3 α4 β6 βCer β4 332 α3 βCer β4 295 β3 βCer β4 34 β3 α3 α2 Type I B antigen βCer β4 170 β3 α3 α4 β6 R βCer β4 365 α3 β3 βCer β4 371 α3 β3 βCer β4 9-0-acetyl GD3 95 α3 α8 Ac-9 βCer β4 9-0-acetyl GT3 96 α3 α8 Ac-9 βCer β4 31 β3 α3 R βCer β4 180 β3 α2 β6 βCer β4 296 β3 βCer β4 302 β3 α3 βCer β4 17 asialo-GM2 βCer β4 GM3 15 α3 βCer β4 81 asialo-GM1 β3 βCer β4 36 β3 α3 α2 α4 BLeb βCer β4 GD3 67 α3 α8 βCer β4 GT3 68 α3 α8 βCer β4 387 β3 HSO3-3 βCer β4 161 β3 α3 α8 βCer β4 Fuc-GD1b 326 α3 α8 α2 βCer β4 disialyl Lea 358 β3 α3 α4 α6 βCer β4 Fuc-GM1 87 α3 β3 α2 βCer β4 179 β3 α2 β6 S S βCer β4 126 GM2α α6 βCer β4 325 β3 HSO3-3 βCer β4 357 β3 HSO3-3 SB1a βCer β4 339 α3 β3 βCer β4 162 β3 α3 α6 βCer β4 GD2 70 α3 α8 βCer β4 GT2 71 α3 α8 βCer β4 197 β3 α3 βCer β4 410 α3 βCer β4 GM2 69 α3 βCer β4 9-0-acetylGT1b 97 α3 α8 β3 9Ac βCer β4 GD1aα 88 α3 β3 α6 βCer β4 198 β3 α6 βCer β4 127 GM1α α6 β3 βCer β4 176 β3 α2 β6 βCer β4 291 β3 βCer β4 349 α3 β3 βCer β4 338 α3 β3 βCer β4 157 β3 α2 βCer β4 GD1b 73 α3 α8 β3 βCer β4 GT1c 74 α3 α8 β3 βCer β4 153 β3 βCer β4 GM1 72 α3 β3 βCer β4 292 β3 βCer β4 290 α3 α8 β3 α6 GQ1aα T βCer β4 159 β3 α3 α2 T βCer β4 345 α3 β3 βCer β4 160 β3 α4 α6 βCer β4 323 α6 β3 α3 βCer β4 177 β3 α2 β6 βCer β4 294 β3 α3 βCer β4 GalNAc-GM1 86 α3 β3 βCer β4 155 β3 βCer β4 158 β3 α3 βCer β4 GT1b 76 α3 α8 β3 βCer β4 GQ1c 77 α3 α8 β3 βCer β4 293 β3 α3 βCer β4 GD1a 75 α3 β3 βCer β4 359 β3 α4 βCer β4 186 β3 α3 β6 βCer β4 GalNAc-GD1a 91 α3 β3 βCer β4 156 β3 α4 βCer β4 178 β3 α2 β6 βCer β4 324 α6 β3 α3 α8 GT1bα βCer β4 82 GM1b β3 α3 βCer β4 84 GD1α β3 α3 α6 βCer β4 GQ1b 78 α3 α8 β3 βCer β4 GP1c 80 α3 α8 β3 βCer β4 Lea 29 β3 α4 U βCer β4 85 β3 α3 U βCer β4 GT1a 79 α3 β3 α8 βCer β4 187 β3 α3 β6 βCer β4 154 β3 α4 βCer β4 183 β3 α3 α2 9Ac α3 β3 β4 βCer β4 188 β3 α3 β6 α2 βCer β4 83 GalNAc-GM1b β3 α3 βCer β4 90 GT1aα β3 α3 α6 β4 βCer βCer β4 335 α3 α8 β3 βCer β4 Gal-GD1b 92 α3 α8 β3 βCer β4 Fuc-GD1b 93 α3 α8 β3 α2 βCer β4 165 β3 α4 βCer β4 128 GD1β α6 β3 α8 α3 βCer β4 305 β3 α3 GalNAc-GD1a βCer β4 209 β3 βCer β4 94 GQ1bα β3 α3 α6 α8 334 βCer β4 189 β3 α3 β6 βCer β4 184 β3 α3 α2 β6 βCer β4 191 β3 α3 α2 β6 V βCer β4 303 β3 α3 GD1a V βCer β4 336 α3 α8 β3 α2 βCer β4 166 β3 α4 α3 βCer β4 182 β3 α4 βCer β4 342 β3 α3 α6 α8 βCer β4 304 β3 α3 α8 www.SphinGOMAP.org βCer β4 344 β3 α3 α6 α8 GQ1β βCer β4 190 β3 α3 β6 α2 βCer β4 327 Sialyl-Lea β3 α3 α4 βCer β4 181 β3 α4 α3 βCer β4 343 β3 α3 α6 α8 βCer β4 167 β3 α4 α2 βCer β4 185 β3 α3 α2 β6 βCer β4 193 β3 α3 α2 β6 βCer β4 330 β3 βCer β4 329 β3 βCer β4 130 GD1c β3 α3 α8 W SphinGOMAP Copyright ©2004 & 2005 Georgia Institute of Technology. All rights Reserved. W βCer β4 192 β3 α3 α2 β6 βCer β4 348 β3 α2 α3 βCer β4 309 β3 α2 βCer β4 311 β3 α2 α3 1. Suzuki, A. (2003) Map 3. Biosynthetic pathways of glycosphingolipids in Handbook of Glycosyltransferases and Related Genes (N. Taniguchi, K. Honke, and M. Fukuda, eds) Springer (Tokyo), pp. 636-646. 2.KEGG Sphingophospholipid biosynthesis: http://www.biologie.uni-hamburg.de/b-online/kegg/kegg/Classes/dblinks_java/map/map00570.html 3. KEGG Sphingolycolipid metabolism: http://www.biologie.uni-hamburg.de/b-online/kegg/kegg/Classes/dblinks_java/map/map00600.html 4. Lipid Bank for Web Database: http://www.lipidbank.jp/ 5. Nomenclature from “Essentials of Glycobiology”as modified for 2nd. Edition: http://grtc.ucsd.edu/symbol.htm *SphinGOMAP is an evolving pathway map for sphingolipid biosynthesis that includes many of the known sphingolipids and glycosphingolipids arranged according to their biosynthetic steps [1-4] or, in the cases where the biosynthetic enzymes have not yet been identified, in hypothetical pathways. It is hoped that this pathway will promote dialog about the “knowns” and “unknowns” of sphingolipid biosynthesis and lead to experiments to refine this model. Users may print or modify the map for personal use if the source is appropriately acknowledged; for other uses, or to recommend corrections or additions, contact Dr. Al Merrill at al.merrill@biology.gatech.edu (please refer to the version of SphinGOMAP and the compounds by molecule number and map coordinates). Additional abbreviations: Gc = N-glycoloyl- (substituted for N-acetyl-); KDN = (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid; IdoA = l-iduronic acid. The choice of monosaccharide symbols is based on the nomenclature of the Consortium of Glycobiology Editors [5]. βCer β4 168 β3 α4 α2 α3 βCer β4 331 β3 α3 191 βCer β4 174 β3 α2 βCer β4 310 β3 α3 βCer β4 347 β3 α3 X βCer β4 346 β3 α3 βCer β4 312 β3 α2 α3 βCer β4 175 β3 α2 α3 X βCer β4 313 β3 α3 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34