| 词条 | Colitose |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443213924 | ImageFile = colitose.png | ImageSize = 180px | ImageAlt = Skeletal formula of colitose | ImageFile1 = Colitose 3D ball.png | ImageAlt1 = Ball-and-stick model of the colitose molecule | IUPACName=(2S,4S,5S)-2,4,5-trihydroxyhexanal | OtherNames= |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo=4221-05-0 | PubChem=6857442 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 5256780 | SMILES = O=C[C@@H](O)C[C@H](O)[C@@H](O)C | InChI = 1/C6H12O4/c1-4(8)6(10)2-5(9)3-7/h3-6,8-10H,2H2,1H3/t4-,5-,6-/m0/s1 | InChIKey = GNTQICZXQYZQNE-ZLUOBGJFBL | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H12O4/c1-4(8)6(10)2-5(9)3-7/h3-6,8-10H,2H2,1H3/t4-,5-,6-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = GNTQICZXQYZQNE-ZLUOBGJFSA-N |Section2={{Chembox Properties | Formula=C6H12O4 | MolarMass = 148.15 g/mol | Appearance= | Density= 1.25 g/mL | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }}Colitose (or GDP-colitose) is a mannose-derived 3,6-dideoxysugar produced by certain bacteria. It is a constituent of the lipopolysaccharide.[1] Biological roleColitose is found in the O-antigen of certain Gram-negative bacteria such as Escherichia coli, Yersinia pseudotuberculosis, Salmonella enterica, Vibrio cholerae, and in marine bacteria such as Pseudoalteromonas sp.[1][2] The sugar was first isolated in 1958,[3] and subsequently was enzymatically synthesized in 1962.[4] BiosynthesisThe resulting product, GDP-L-colitose, is then incorporated into the O-antigen by glycosyltransferases and O-antigen processing proteins. Further reactions join the O-antigen to the core polysaccharide to form the full lipopolysaccharide. GDP-4-keto-6-deoxymannose-3-dehydratase (ColD)ColD is a PLP-dependent enzyme responsible for the removal of the C-3' hydroxyl group during the biosynthesis of GDP-colitose.[5] It is a product of the Wbdk or ColD genes in Escherichia coli O55 or Salmonella enterica, respectively, and is commonly referred to as ColD.[1] Usage in biotechnologyAlthough the sugar is relatively rare, recent work with glycosyltransferases suggests that obscure sugars such as colitose can be incorporated into existing natural-product scaffolds, thereby constructing novel and potentially therapeutic compounds.[6] References1. ^1 2 {{cite journal |vauthors=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydrate Research |volume=338 |issue=23 |pages=2503–19 |date=November 2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}} 2. ^{{cite journal |vauthors=Muldoon J, Perepelov AV, Shashkov AS |title=Structure of a colitose-containing O-specific polysaccharide of the marine bacterium Pseudoalteromonas tetraodonis IAM 14160(T) |journal=Carbohydrate Research |volume=333 |issue=1 |pages=41–6 |date=June 2001 |pmid=11423109 |doi=10.1016/S0008-6215(01)00121-5|display-authors=etal}} 3. ^{{cite journal |vauthors=Luderitz O, Staub AM, Stirm S, Westphal O |title=[Colitose, 3-desoxy-L-fucose, a new sugar building block with immunospecific functions in the endotoxins, lipopolysaccharides, of some gram-negative bacteria.] |language=German |journal=Biochemische Zeitschrift |volume=330 |issue=3 |pages=193–7 |year=1958 |pmid=13546193}} 4. ^{{cite journal |vauthors=Heath EC, ELBEIN AD |title=The enzymatic synthesis of guanosine diphosphate colitose by a mutant strain of Escherichia coli |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=48 |issue= |pages=1209–16 |date=July 1962 |pmid=13905784 |pmc=220934 |doi=10.1073/pnas.48.7.1209}} 5. ^1 {{cite journal |vauthors=Alam J, Beyer N, Liu HW |title=Biosynthesis of colitose: expression, purification, and mechanistic characterization of GDP-4-keto-6-deoxy-D-mannose-3-dehydrase (ColD) and GDP-L-colitose synthase (ColC) |journal=Biochemistry |volume=43 |issue=51 |pages=16450–60 |date=December 2004 |pmid=15610039 |doi=10.1021/bi0483763}} 6. ^{{cite journal |vauthors=Zhang C, Griffith BR, Fu Q |title=Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions |journal=Science |volume=313 |issue=5791 |pages=1291–4 |date=September 2006 |pmid=16946071 |doi=10.1126/science.1130028|display-authors=etal}} 2 : Deoxy sugars|Aldohexoses |
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