MetaCyc Compound: 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate

Synonyms: Leg5Ac7Ac, N, N'-diacetyllegionaminate, N, N'-diacetyllegionaminic acid, 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonic acid

Superclasses: all carbohydratesa carbohydratea glycana carbohydrate derivative

5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate is a nonulosonate derivative with the same stereochemistry as sialic acid, but with added features of 9-deoxy and 7-amino groups.

Bacteria incorporate derivatives of 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate into virulence-associated cell surface glycoconjugates which may include lipopolysaccharide (LPS), capsular polysaccharide, pili and flagella.

5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate was first identified in 1994 as a component of Legionella pneumophila serogroup 1 (the causative agent of Legionnaires' disease) LPS [Knirel94], and subsequently reported from several other organisms, including Pseudomonas fluorescens strain ATCC 49271 [Knirel96], Aliivibrio salmonicida [Edebrink96], Vibrio alginolyticus [Nazarenko90], and Acinetobacter baumannii [Haseley97]. In all cases the reported stereochemistry was originally incorrect, and the correct stereochemistry was determined only in 2001 [Tsvetkov01].

Citations: [Glaze08]

Chemical Formula: C13H21N2O8

Molecular Weight: 333.32 Daltons

Monoisotopic Molecular Weight: 334.1376156934 Daltons

5,7-diacetamido-3,5,7,9-tetradeoxy-D-<i>glycero</i>-D-<i>galacto</i>-nonulopyranosonate compound structure

SMILES: CC(O)C(NC(=O)C)[CH]1(OC(C(=O)[O-])(O)CC(O)C(NC(C)=O)1)

InChI: InChI=1S/C13H22N2O8/c1-5(16)9(14-6(2)17)11-10(15-7(3)18)8(19)4-13(22,23-11)12(20)21/h5,8-11,16,19,22H,4H2,1-3H3,(H,14,17)(H,15,18)(H,20,21)/p-1/t5-,8+,9-,10-,11+,13+/m1/s1


Unification Links: ChEBI:68669, PubChem:70678926

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -69.13852Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

CMP-legionaminate biosynthesis I , CMP-legionaminate biosynthesis II :
CTP + 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate → CMP-N,N'-diacetyllegionaminate + diphosphate

Reactions known to produce the compound:

CMP-legionaminate biosynthesis I , CMP-legionaminate biosynthesis II :
2,4-diacetamido-2,4,6-trideoxy-α-D-mannopyranose + phosphoenolpyruvate + H2O → 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulopyranosonate + phosphate

Created 11-Mar-2011 by Fulcher CA, SRI International
Revised 14-Aug-2012 by Caspi R, SRI International


Angata02: Angata T, Varki A (2002). "Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective." Chem Rev 102(2);439-69. PMID: 11841250

Cox02: Cox AD, Hood DW, Martin A, Makepeace KM, Deadman ME, Li J, Brisson JR, Moxon ER, Richards JC (2002). "Identification and structural characterization of a sialylated lacto-N-neotetraose structure in the lipopolysaccharide of Haemophilus influenzae." Eur J Biochem 269(16);4009-19. PMID: 12180977

Edebrink96: Edebrink P, Jansson PE, Bogwald J, Hoffman J (1996). "Structural studies of the Vibrio salmonicida lipopolysaccharide." Carbohydr Res 287(2);225-45. PMID: 8766209

Glaze08: Glaze PA, Watson DC, Young NM, Tanner ME (2008). "Biosynthesis of CMP-N,N'-diacetyllegionaminic acid from UDP-N,N'-diacetylbacillosamine in Legionella pneumophila." Biochemistry 47(10);3272-82. PMID: 18275154

Haseley97: Haseley SR, Wilkinson SG (1997). "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid." Eur J Biochem 250(2);617-23. PMID: 9428717

Hood99: Hood DW, Makepeace K, Deadman ME, Rest RF, Thibault P, Martin A, Richards JC, Moxon ER (1999). "Sialic acid in the lipopolysaccharide of Haemophilus influenzae: strain distribution, influence on serum resistance and structural characterization." Mol Microbiol 33(4);679-92. PMID: 10447878

Knirel94: Knirel YA, Rietschel ET, Marre R, Zahringer U (1994). "The structure of the O-specific chain of Legionella pneumophila serogroup 1 lipopolysaccharide." Eur J Biochem 221(1);239-45. PMID: 8168511

Knirel96: Knirel YA, Helbig JH, Zahringer U (1996). "Structure of a decasaccharide isolated by mild acid degradation and dephosphorylation of the lipopolysaccharide of Pseudomonas fluorescens strain ATCC 49271." Carbohydr Res 283;129-39. PMID: 8901267

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Nazarenko90: Nazarenko EL, Shashkov AS, Knirel' IuA, Ivanova EP, Ovodov IuS (1990). "[Uncommon acidic monosaccharides--components of O-specific polysaccharides of Vibrio bacteria]." Bioorg Khim 16(10);1426-9. PMID: 1707620

Severi05: Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH (2005). "Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter." Mol Microbiol 58(4);1173-85. PMID: 16262798

Severi08: Severi E, Muller A, Potts JR, Leech A, Williamson D, Wilson KS, Thomas GH (2008). "Sialic acid mutarotation is catalysed by the Escherichia coli beta -propeller protein YJHT." J Biol Chem 283(8):4841-9. PMID: 18063573

Tsvetkov01: Tsvetkov YE, Shashkov AS, Knirel YA, Zahringer U (2001). "Synthesis and identification in bacterial lipopolysaccharides of 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids." Carbohydr Res 331(3);233-7. PMID: 11383892

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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