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Volumn 67, Issue 5, 2014, Pages 405-414

Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins

Author keywords

4 amino 4 deoxyheptose; Biosynthetic pathway; Septacidin; Spicamycin; Synthesis

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; GLYCOSIDE; HEPTOSE; SEPTACIDIN; SEPTACIDIN 4 AMINOHEPTOSE; SPICAMYCIN; UNCLASSIFIED DRUG;

EID: 84901480088     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2014.15     Document Type: Article
Times cited : (10)

References (35)
  • 1
    • 84876911163 scopus 로고
    • Septacidin a new antitumor and antifungal antibiotic produced by Streptomyces fimbriatus
    • Dutcher, J. D., Von Saltza, M. H. & Pansy, F. E. Septacidin, a new antitumor and antifungal antibiotic produced by Streptomyces fimbriatus. Antimicrob. Agents Chemother. 161, 83-88 (1963
    • (1963) Antimicrob. Agents Chemother , vol.161 , pp. 83-88
    • Dutcher, J.D.1    Von Saltza, M.H.2    Pansy, F.E.3
  • 2
    • 0021033184 scopus 로고
    • Studies on the differentiation inducers of myeloid leukemic cells III. Spicamycin, a new inducer of differentiation of HL-60 human promyelocytic leukemia cells
    • Hayakawa, Y. et al. Studies on the differentiation inducers of myeloid leukemic cells. III. Spicamycin, a new inducer of differentiation of HL-60 human promyelocytic leukemia cells. J. Antibiot. 36, 934-937 (1983
    • (1983) J. Antibiot , vol.36 , pp. 934-937
    • Hayakawa, Y.1
  • 3
    • 0022244817 scopus 로고
    • Spicamycin, a new differentiation inducer of mouse myeloid leukemia cells (Ml) and human promyelocytic leukemia cells (HL-60)
    • Hayakawa, Y. et al. Spicamycin, a new differentiation inducer of mouse myeloid leukemia cells (Ml) and human promyelocytic leukemia cells (HL-60). Agric. Biol. Chem. 49, 2685-2691 (1985
    • (1985) Agric. Biol. Chem , vol.49 , pp. 2685-2691
    • Hayakawa, Y.1
  • 4
    • 0027493092 scopus 로고
    • Structure-Antitumor activity relationship of semi-synthetic spicamycin analogues
    • Kamishohara, M. et al. Structure-Antitumor activity relationship of semi-synthetic spicamycin analogues. J. Antibiot. 46, 1439-1446 (1993
    • (1993) J. Antibiot , vol.46 , pp. 1439-1446
    • Kamishohara, M.1
  • 5
    • 84859218108 scopus 로고    scopus 로고
    • A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: A placebo-controlled, proof-of-concept trial
    • Weinstein, S.M.et al. A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: A placebo-controlled, proof-of-concept trial. J. Pain Sympt. Manage. 43, 679-693 (2012
    • (2012) J. Pain Sympt. Manage , vol.43 , pp. 679-693
    • Weinstein, S.M.1
  • 6
    • 0000510741 scopus 로고
    • Nuclear magnetic resonance spectroscopy of acetylated methyl glycopyranosides of aminohexoses characterization of an aminohexose from septacidin
    • Agahigian, H. et al. Nuclear magnetic resonance spectroscopy of acetylated methyl glycopyranosides of aminohexoses. Characterization of an aminohexose from septacidin. J. Org. Chem. 30, 1085-1088 (1965
    • (1965) J. Org. Chem , vol.30 , pp. 1085-1088
    • Agahigian, H.1
  • 7
    • 0029160128 scopus 로고
    • Absolute configuration of spicamycin, an antitumor antibiotic produced by Streptomyces alanosinicus
    • Sakai, T. et al. Absolute configuration of spicamycin, an antitumor antibiotic produced by Streptomyces alanosinicus. J. Antibiot. 48, 899-900 (1995
    • (1995) J. Antibiot , vol.48 , pp. 899-900
    • Sakai, T.1
  • 8
    • 21044441721 scopus 로고    scopus 로고
    • Anicemycin, a new inhibitor of anchorage-independent growth of tumor cells from streptomyces sp tp-A0648
    • Igarashi, Y. et al. Anicemycin, a new inhibitor of anchorage-independent growth of tumor cells from Streptomyces sp. TP-A0648. J. Antibiot. 58, 322-326 (2005
    • (2005) J. Antibiot , vol.58 , pp. 322-326
    • Igarashi, Y.1
  • 9
    • 0037012864 scopus 로고    scopus 로고
    • Total synthesis of spicamycin
    • Suzuki, T. et al. Total synthesis of spicamycin. J. Org. Chem. 67, 2874-2880 (2002
    • (2002) J. Org. Chem , vol.67 , pp. 2874-2880
    • Suzuki, T.1
  • 10
    • 0033605936 scopus 로고    scopus 로고
    • Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines: Synthesis of 6-(b-d-mannopyranosylamino)-9hpurine and its b-d-gluco isomer n-glycoside models for spicamycin and septacidin
    • Chida, N., Suzuki, T., Tanaka, S. & Yamada, I. Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines: Synthesis of 6-(b-D-mannopyranosylamino)-9Hpurine and its b-D-gluco isomer, N-glycoside models for spicamycin and septacidin. Tetrahedron Lett. 40, 2573-2576 (1999
    • (1999) Tetrahedron Lett , vol.40 , pp. 2573-2576
    • Chida, N.1    Suzuki, T.2    Tanaka, S.3    Yamada, I.4
  • 11
  • 12
    • 0033580751 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin
    • Martín, A., Butters, T. D. & Fleet, G. W. J. Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin. Tetrahedron 10, 2343-2360 (1999
    • (1999) Tetrahedron , vol.10 , pp. 2343-2360
    • Martín, A.1    Butters, T.D.2    Fleet, G.W.J.3
  • 13
    • 0344550546 scopus 로고    scopus 로고
    • An approach to the generation of simple analogues of the antitumor agent spicamycin
    • Mons, S. & Fleet, G. W. J. An approach to the generation of simple analogues of the antitumor agent spicamycin. Org. Biomol. Chem. 1, 3685-3691 (2003
    • (2003) Org. Biomol. Chem , vol.1 , pp. 3685-3691
    • Mons, S.1    Fleet, G.W.J.2
  • 14
    • 84870525100 scopus 로고    scopus 로고
    • Easy access to L-mannosides and L-galactosides by using C-H activation of the corresponding 6-deoxysugars
    • Frihed, T. G., Heuckendorff, M., Pedersen, C. M. & Bols, M. Easy access to L-mannosides and L-galactosides by using C-H activation of the corresponding 6-deoxysugars. Angew Chem. Int. Ed. 51, 12285-12288 (2012
    • (2012) Angew Chem. Int. E.d. , vol.51 , pp. 12285-12288
    • Frihed, T.G.1    Heuckendorff, M.2    Pedersen, C.M.3    Bols, M.4
  • 15
    • 0030061084 scopus 로고    scopus 로고
    • Decarboxylation of a sialic acid derivative
    • Potter, J. J. & von Itzstein, M. Decarboxylation of a sialic acid derivative. Carbohydr. Res. 282, 181-187 (1996
    • (1996) Carbohydr. Res , vol.282 , pp. 181-187
    • Potter, J.J.1    Von Itzstein, M.2
  • 16
    • 39849091032 scopus 로고    scopus 로고
    • Investigation into an efficient synthesis of 2, 3-dehydro-N-Acetyl neuraminic acid leads to three decarboxylated sialic acid dimmers
    • Horn, E. J., Saludes, J. P. & Gervay-Hague, J. Investigation into an efficient synthesis of 2, 3-dehydro-N-Acetyl neuraminic acid leads to three decarboxylated sialic acid dimmers. Carbohydr. Res. 343, 936-940 (2008
    • (2008) Carbohydr. Res , vol.343 , pp. 936-940
    • Horn, E.J.1    Saludes, J.P.2    Gervay-Hague, J.3
  • 17
    • 80455129357 scopus 로고    scopus 로고
    • A practical synthesis of zanamivir phosphonate congeners with potent anti-influenza activity
    • Shie, J-J. et al. A practical synthesis of zanamivir phosphonate congeners with potent anti-influenza activity. J. Am. Chem. Soc. 133, 17959-17965 (2011
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 17959-17965
    • Shie, J.-J.1
  • 18
    • 37049092550 scopus 로고
    • New and improved methods for the radical decarboxylation of acids
    • Barton, D. H. R., Crich, D. & Motherwell, W. B. New and improved methods for the radical decarboxylation of acids. J. Chem. Soc. Chem. Commun. 1983, 939-941 (1983
    • (1983) J. Chem. Soc. Chem. Commun , vol.1983 , pp. 939-941
    • Barton, D.H.R.1    Crich, D.2    Motherwell, W.B.3
  • 19
    • 0007698991 scopus 로고
    • Stereoselective free radical reactions in the preparation of 2-deoxy-b-D-glucosides
    • Crich, D. & Ritchie, T. J. Stereoselective free radical reactions in the preparation of 2-deoxy-b-D-glucosides. J. Chem. Soc. Chem. Commun. 1988, 1461-1463 (1988
    • (1988) J. Chem. Soc. Chem. Commun , vol.1988 , pp. 1461-1463
    • Crich, D.1    Ritchie, T.J.2
  • 20
    • 33646913654 scopus 로고    scopus 로고
    • Studies on the alpha-(1-4)- and alpha-(1-8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides
    • Ando, H. et al. Studies on the alpha-(1-4)- and alpha-(1-8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides. Carbohydr. Res. 341, 1522-1532 (2006
    • (2006) Carbohydr. Res , Issue.341 , pp. 1522-1532
    • Ando, H.1
  • 21
    • 0013624593 scopus 로고
    • Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide
    • Parikh, J. R. & v. E. Doering, W. Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide. J. Am. Chem. Soc. 89, 5505-5507 (1967
    • (1967) J. Am. Chem. Soc , Issue.89 , pp. 5505-5507
    • Parikh J.R.V E. Doering, W.1
  • 22
    • 0003032001 scopus 로고
    • Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides: The moffatt swern, and related oxidations
    • Tidwell, T. T. Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides: The Moffatt, Swern, and related oxidations. Org. React. 39, 297-572 (1990
    • (1990) Org. React , vol.39 , pp. 297-572
    • Tidwell, T.T.1
  • 24
    • 37049087517 scopus 로고
    • Diastereoselective free-radical reactions Part 1. Preparation of 2-deoxy-b-glycosides by synthesis and reductive decarboxylation of 3-deoxyulosonic acid glycosides
    • Crich, D. & Ritchie, T. J. Diastereoselective free-radical reactions. Part 1. Preparation of 2-deoxy-b-glycosides by synthesis and reductive decarboxylation of 3-deoxyulosonic acid glycosides. J. Chem. Soc. Perkin Trans. 1, 945-954 (1990
    • (1990) J. Chem. Soc. Perkin Trans , vol.1 , pp. 945-954
    • Crich, D.1    Ritchie, T.J.2
  • 25
    • 37049077638 scopus 로고
    • Diastereoselective free-radical reactions Part 2. Synthesis of 2-deoxy-b-C-pyranosides by diastereoselective hydrogen-Atom transfer
    • Crich, D. & Lim, L. B. L. Diastereoselective free-radical reactions. Part 2. Synthesis of 2-deoxy-b-C-pyranosides by diastereoselective hydrogen-Atom transfer. J. Chem. Soc. Perkin Trans. 1, 2209-2214 (1991
    • (1991) J. Chem. Soc. Perkin Trans , vol.1 , pp. 2209-2214
    • Crich, D.1    Lim, L.B.L.2
  • 26
    • 8644274772 scopus 로고    scopus 로고
    • Acylic sugar derivatives for GC/MS analysis of 13C enrichment during carbohydrate metabolism
    • Price, N. P. J. Acylic sugar derivatives for GC/MS analysis of 13C enrichment during carbohydrate metabolism. Anal. Chem. 76, 6566-6574 (2004
    • (2004) Anal. Chem , vol.76 , pp. 6566-6574
    • Price, N.P.J.1
  • 27
    • 84876915300 scopus 로고    scopus 로고
    • The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars
    • Lin, C-I., McCarty, R. M. & Liu, H-W. The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars. Chem. Soc. Rev. 42, 4377-4407 (2013
    • (2013) Chem. Soc. Rev , vol.42 , pp. 4377-4407
    • Lin, C.-I.1    McCarty, R.M.2    Liu, H.-W.3
  • 28
    • 0037144487 scopus 로고    scopus 로고
    • Biosynthesis of tunicamycin and metabolic origin of the 11-carbon dialdose sugar, tunicamine
    • Tsvetanova, B. C., Kiemle, D. J. & Price, N. P. J. Biosynthesis of tunicamycin and metabolic origin of the 11-carbon dialdose sugar, tunicamine. J. Biol. Chem. 277, 35289-35296 (2002
    • (2002) J. Biol. Chem , vol.277 , pp. 35289-35296
    • Tsvetanova, B.C.1    Kiemle, D.J.2    Price, N.P.J.3
  • 29
    • 0017520243 scopus 로고
    • Mass spectrometric studies of twenty-one metabolically important acylglycines
    • Ramsdell, H. S., Baretz, B. H. & Tanaka, K. Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed. Mass Spectrom. 4, 220-225 (1977
    • (1977) Biomed. Mass Spectrom , vol.4 , pp. 220-225
    • Ramsdell, H.S.1    Baretz, B.H.2    Tanaka, K.3
  • 30
    • 3242745131 scopus 로고    scopus 로고
    • The mechanism of the reaction catalyzed by ADP-beta-L-glycero-D-manno- heptose 6-epimerase
    • Read, J. A., Ahmed, R. A., Morrison, J. P., Coleman, Jr W. G. & Tanner, M. E. The mechanism of the reaction catalyzed by ADP-beta-L-glycero-D- manno-heptose 6-epimerase. J. Am. Chem. Soc. 126, 8878-8879 (2004
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 8878-8879
    • Read, J.A.1    Ahmed, R.A.2    Morrison, J.P.3    Coleman Jr., W.G.4    Tanner, M.E.5
  • 31
    • 0015103047 scopus 로고
    • Lipopolysaccharide and aldoheptose biosynthesis in transketolase mutants of Salmonella typhimurium
    • Eidels, L. & Osborn, M. J. Lipopolysaccharide and aldoheptose biosynthesis in transketolase mutants of Salmonella typhimurium. Proc. Natl Acad. Sci. USA 68, 1673-1677 (1971
    • (1971) Proc. Natl Acad. Sci. USA , vol.68 , pp. 1673-1677
    • Eidels, L.1    Osborn, M.J.2
  • 32
    • 0036135690 scopus 로고    scopus 로고
    • Biosynthesis pathway of ADP-L-glycero-beta-D-manno-heptose in Escherichia coli
    • Kneidinger, B. et al. Biosynthesis pathway of ADP-L-glycero-beta-D-manno- heptose in Escherichia coli. J. Bacteriol. 184, 363-369 (2002
    • (2002) J. Bacteriol , vol.184 , pp. 363-369
    • Kneidinger, B.1
  • 34
    • 84865463329 scopus 로고    scopus 로고
    • Complete 6-deoxy-D-Altroheptose biosynthesis pathway from Campylobacter jejuni: More complex than anticipated
    • McCallum, M., Shaw, S. D., Shaw, G. S. & Creuzenet, C. Complete 6-deoxy-D-Altroheptose biosynthesis pathway from Campylobacter jejuni: More complex than anticipated. J. Biol. Chem. 287, 29776-29788 (2012
    • (2012) J. Biol. Chem , vol.287 , pp. 29776-29788
    • McCallum, M.1    Shaw, S.D.2    Shaw, G.S.3    Creuzenet, C.4
  • 35
    • 84880053066 scopus 로고    scopus 로고
    • Comparison of predicted epimerases and reductases of the Campylobacter jejuni D-Altro- and L-gluco-heptose synthesis pathways
    • McCallum, M., Shaw, G. S. & Creuzenet, C. Comparison of predicted epimerases and reductases of the Campylobacter jejuni D-Altro- and L-gluco-heptose synthesis pathways. J. Biol. Chem. 288, 19569-19580 (2013
    • (2013) J. Biol. Chem , vol.288 , pp. 19569-19580
    • McCallum, M.1    Shaw, G.S.2    Creuzenet, C.3


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