GDP-beta-L-fucose (CHEBI:13332)

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CHEBI:13332 - GDP-β-L-fucose

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ChEBI Name	GDP-β-L-fucose

ChEBI ID	CHEBI:13332

ChEBI ASCII Name	GDP-beta-L-fucose

Definition	A GDP-L-fucose in which the anomeric oxygen is on the same side of the fucose ring as the methyl substituent.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000008551145

Download	Molfile XML SDF

more structures >>

Molfile

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The Resolver thinks Mol

GFB - Ideal conformer

Mrv1927 06082115203D

starting HoverWatcher_5

Time for openFile(GFB - Ideal conformer

Mrv1927 06082115203D

63 66 0 0 0 0 999 V2000

0.6540 1.8230 2.6090 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0290 1.9670 1.0490 P 0 0 1 0 0 5 0 0 0 0 0 0

1.5030 3.3440 0.7820 O 0 0 0 0 0 0 0 0 0 0 0 0

2.1910 0.9180 0.6770 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2740 1.6650 0.1540 O 0 0 0 0 0 0 0 0 0 0 0 0

3.7750 0.8570 0.9590 P 0 0 1 0 0 5 0 0 0 0 0 0

-1.4420 2.4890 0.1750 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.4850 1.9190 -0.7880 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.9510 0.6470 -0.3080 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7050 2.8590 -0.8540 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.3440 0.5430 -0.6740 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.9010 3.3320 -2.1880 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.8930 1.9680 -0.4150 C 0 0 2 0 0 0 0 0 0 0 0 0

-6.0470 2.2240 -1.2200 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.0280 -0.4360 0.1750 N 0 0 0 0 0 0 0 0 0 0 0 0

-4.6450 -0.8280 1.4250 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.1710 -1.1200 -0.1370 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.4820 -1.7100 1.8870 N 0 0 0 0 0 0 0 0 0 0 0 0

-6.4510 -1.9340 0.9660 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.5950 -2.7650 0.9210 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.8770 -3.4910 1.8600 O 0 0 0 0 0 0 0 0 0 0 0 0

-8.3670 -2.7350 -0.1870 N 0 0 0 0 0 0 0 0 0 0 0 0

-8.0430 -1.9200 -1.2300 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.8460 -1.9090 -2.3430 N 0 0 0 0 0 0 0 0 0 0 0 0

-6.9830 -1.1430 -1.2010 N 0 0 0 0 0 0 0 0 0 0 0 0

5.8830 -0.3400 -0.1660 C 0 0 1 0 0 0 0 0 0 0 0 0

6.2730 -0.6970 -1.6030 C 0 0 2 0 0 0 0 0 0 0 0 0

4.4690 -0.1490 -0.0900 O 0 0 0 0 0 0 0 0 0 0 0 0

6.2680 -1.4030 0.7090 O 0 0 0 0 0 0 0 0 0 0 0 0

7.7810 -0.9590 -1.6640 C 0 0 1 0 0 0 0 0 0 0 0 0

5.9410 0.3880 -2.4710 O 0 0 0 0 0 0 0 0 0 0 0 0

8.1360 -2.0710 -0.6720 C 0 0 1 0 0 0 0 0 0 0 0 0

8.1430 -1.3630 -2.9860 O 0 0 0 0 0 0 0 0 0 0 0 0

7.6740 -1.6610 0.7290 C 0 0 2 0 0 0 0 0 0 0 0 0

7.4790 -3.2810 -1.0560 O 0 0 0 0 0 0 0 0 0 0 0 0

7.9700 -2.7920 1.7160 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3570 2.2090 0.8040 O 0 0 0 0 0 0 0 0 0 0 0 0

4.0340 0.3300 2.4590 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8530 2.5110 1.1840 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1780 3.5010 -0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0500 1.8040 -1.7810 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5800 3.6950 -0.1660 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.4450 0.2740 -1.7250 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6560 3.9280 -2.2870 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.1180 2.1130 0.6420 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.3740 3.1320 -1.1600 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7760 -0.4610 1.9520 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.1560 -3.2960 -0.2410 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3900 0.5770 0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7350 -1.5920 -1.9140 H 0 0 0 0 0 0 0 0 0 0 0 0

8.3200 -0.0490 -1.4000 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0010 0.6120 -2.4790 H 0 0 0 0 0 0 0 0 0 0 0 0

9.2150 -2.2260 -0.6690 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9400 -0.7060 -3.6670 H 0 0 0 0 0 0 0 0 0 0 0 0

8.2040 -0.7610 1.0380 H 0 0 0 0 0 0 0 0 0 0 0 0

7.6600 -4.0290 -0.4700 H 0 0 0 0 0 0 0 0 0 0 0 0

7.6410 -2.5000 2.7130 H 0 0 0 0 0 0 0 0 0 0 0 0

7.4390 -3.6920 1.4070 H 0 0 0 0 0 0 0 0 0 0 0 0

9.0420 -2.9900 1.7300 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.6280 -1.3340 -3.0930 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.6320 -2.4770 -2.3790 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3350 0.9440 2.8560 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6790 -0.5530 2.6320 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 1 0 0 0

1 62 1 0 0 0 0

3 2 2 0 0 0 0

2 5 1 0 0 0 0

2 4 1 0 0 0 0

6 4 1 6 0 0 0

5 7 1 0 0 0 0

28 6 1 0 0 0 0

37 6 2 0 0 0 0

6 38 1 0 0 0 0

8 7 1 0 0 0 0

7 40 1 0 0 0 0

7 39 1 0 0 0 0

8 41 1 6 0 0 0

10 8 1 0 0 0 0

8 9 1 0 0 0 0

9 11 1 0 0 0 0

12 10 1 0 0 0 0

10 13 1 0 0 0 0

10 42 1 1 0 0 0

13 11 1 0 0 0 0

11 43 1 6 0 0 0

11 15 1 0 0 0 0

44 12 1 0 0 0 0

14 13 1 0 0 0 0

13 45 1 1 0 0 0

14 46 1 0 0 0 0

15 17 1 0 0 0 0

15 16 1 0 0 0 0

47 16 1 0 0 0 0

16 18 2 0 0 0 0

25 17 1 0 0 0 0

17 19 2 0 0 0 0

19 18 1 0 0 0 0

19 20 1 0 0 0 0

22 20 1 0 0 0 0

20 21 2 0 0 0 0

23 22 1 0 0 0 0

22 48 1 0 0 0 0

25 23 2 0 0 0 0

24 23 1 0 0 0 0

60 24 1 0 0 0 0

24 61 1 0 0 0 0

27 26 1 0 0 0 0

26 29 1 0 0 0 0

26 49 1 1 0 0 0

26 28 1 0 0 0 0

30 27 1 0 0 0 0

31 27 1 0 0 0 0

27 50 1 6 0 0 0

34 29 1 0 0 0 0

33 30 1 0 0 0 0

30 51 1 1 0 0 0

30 32 1 0 0 0 0

52 31 1 0 0 0 0

32 53 1 1 0 0 0

35 32 1 0 0 0 0

32 34 1 0 0 0 0

54 33 1 0 0 0 0

34 55 1 1 0 0 0

34 36 1 0 0 0 0

35 56 1 0 0 0 0

57 36 1 0 0 0 0

58 36 1 0 0 0 0

36 59 1 0 0 0 0

38 63 1 0 0 0 0

M END): 24 ms

reading 63 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

63 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C16H25N5O15P2

Net Charge

Average Mass

589.344

Monoisotopic Mass

589.08224

InChI

InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15+/m0/s1

InChIKey

LQEBEXMHBLQMDB-JGQUBWHWSA-N

SMILES

C[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:txid3702)	See: DOI

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	GDP-β-L-fucose (CHEBI:13332) has role mouse metabolite (CHEBI:75771) GDP-β-L-fucose (CHEBI:13332) has role plant metabolite (CHEBI:76924) GDP-β-L-fucose (CHEBI:13332) is a GDP-L-fucose (CHEBI:17009) GDP-β-L-fucose (CHEBI:13332) is conjugate acid of GDP-β-L-fucose(2−) (CHEBI:57273)

Incoming	GDP-β-L-fucose(2−) (CHEBI:57273) is conjugate base of GDP-β-L-fucose (CHEBI:13332)

IUPAC Name

guanosine 5'-[3-(6-deoxy-β-L-galactopyranosyl) dihydrogen diphosphate]

Synonym	Source
GDP-beta-L-fucose	KEGG COMPOUND

Manual Xrefs	Databases
C00325	KEGG COMPOUND
GFB	PDBeChem
View more database links

Registry Numbers	Types	Sources
15839-70-0	CAS Registry Number	ChemIDplus
75468	Reaxys Registry Number	Reaxys

Citations

McMillan BJ, Zimmerman B, Egan ED, Lofgren M, Xu X, Hesser A, Blacklow SC (2017)
Structure of human POFUT1, its requirement in ligand-independent oncogenic Notch signaling, and functional effects of Dowling-Degos mutations.
Glycobiology 27, 777-786 [PubMed:28334865]
[show Abstract]

Li Z, Han K, Pak JE, Satkunarajah M, Zhou D, Rini JM (2017)
Recognition of EGF-like domains by the Notch-modifying O-fucosyltransferase POFUT1.
Nature chemical biology 13, 757-763 [PubMed:28530709]
[show Abstract]

Allen JG, Mujacic M, Frohn MJ, Pickrell AJ, Kodama P, Bagal D, San Miguel T, Sickmier EA, Osgood S, Swietlow A, Li V, Jordan JB, Kim KW, Rousseau AC, Kim YJ, Caille S, Achmatowicz M, Thiel O, Fotsch CH, Reddy P, McCarter JD (2016)
Facile Modulation of Antibody Fucosylation with Small Molecule Fucostatin Inhibitors and Cocrystal Structure with GDP-Mannose 4,6-Dehydratase.
ACS chemical biology 11, 2734-2743 [PubMed:27434622]
[show Abstract]

Chen CI, Keusch JJ, Klein D, Hess D, Hofsteenge J, Gut H (2012)
Structure of human POFUT2: insights into thrombospondin type 1 repeat fold and O-fucosylation.
The EMBO journal 31, 3183-3197 [PubMed:22588082]
[show Abstract]

Lira-Navarrete E, Valero-González J, Villanueva R, Martínez-Júlvez M, Tejero T, Merino P, Panjikar S, Hurtado-Guerrero R (2011)
Structural insights into the mechanism of protein O-fucosylation.
PloS one 6, e25365 [PubMed:21966509]
[show Abstract]

Albermann C, Piepersberg W, Wehmeier UF (2001)
Synthesis of the milk oligosaccharide 2'-fucosyllactose using recombinant bacterial enzymes.
Carbohydrate research 334, 97-103 [PubMed:11502265]
[show Abstract]

Albermann C, Distler J, Piepersberg W (2000)
Preparative synthesis of GDP-beta-L-fucose by recombinant enzymes from enterobacterial sources.
Glycobiology 10, 875-881 [PubMed:10988249]
[show Abstract]

Druzhinina TN, Utkina NS, Chan K, Strecker G, Shibaev VN (1999)
Activity of enzymes catalyzing formation of beta-L-fucosyl phosphate and GDP-beta-L-fucose in amphibian tissues and their application in chemo-enzymic synthesis of GDP-beta-L-fucose.
Biochemistry. Biokhimiia 64, 783-787 [PubMed:10424902]
[show Abstract]

Adelhorst K, Whitesides GM (1993)
Large-scale synthesis of beta-L-fucopyranosyl phosphate and the preparation of GDP-beta-L-fucose.
Carbohydrate research 242, 69-76 [PubMed:8495447]
[show Abstract]

Last Modified

08 June 2021

CHEBI:13332 - GDP-β-L-fucose

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