Calicheamicin (English Wikipedia)

Maiese, William M; Lechevalier, Mary P; Lechevalier, Hubert A; Korshalla, Joseph; Kuck, Nydia; Fantini, Amadeo; Wildey, Mary Jo; Thomas, John; Greenstein, Michael (April 1989). "Calicheamicins, a novel family of antitumor antibiotics: taxonomy, fermentation and biological properties". Journal of Antibiotics. 42 (4): 558–63. doi:10.7164/antibiotics.42.558. PMID 2722671.
Lee, May D.; Manning, Joann K.; Williams, David R.; Kuck, Nydia A.; Testa, Raymond T.; Borders, Donald B. (July 1989). "Calichemicins, a novel family of antitumor antibiotics. 3. Isolation, purification and characterization of calichemicins β1Br, γ1Br, α2I, α3I, β1I, γ1I, and Δ1I". Journal of Antibiotics. 42 (7): 1070–87. doi:10.7164/antibiotics.42.1070. PMID 2753814.
G.A. Ellestad (2011). "Structural and Conformational Features Relevant to the Anti-Tumor Activity of Calichemicin γ1I". Chirality. 23 (8): 660–671. doi:10.1002/chir.20990. PMID 21800378.
S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC 49132. PMID 1584797.
Simkhada D, Oh TJ, Kim EM, Yoo JC, Sohng JK (January 2009). "Cloning and characterization of CalS7 from Micromonospora echinospora sp. calichensis as a glucose-1-phosphate nucleotidyltransferase". Biotechnol. Lett. 31 (1): 147–53. doi:10.1007/s10529-008-9844-9. PMID 18807197. S2CID 2115227.
Zhang C, Bitto E, Goff RD, Singh S, Bingman CA, Griffith BR, Albermann C, Phillips GN Jr, Thorson JS (Aug 25, 2008). "Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis". Chem. Biol. 15 (8): 842–53. doi:10.1016/j.chembiol.2008.06.011. PMC 2965851. PMID 18721755.
Horsman, GP; Chen, Y; Thorson, JS; Shen, B (Jun 22, 2010). "Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes". Proc Natl Acad Sci U S A. 107 (25): 11331–5. Bibcode:2010PNAS..10711331H. doi:10.1073/pnas.1003442107. PMC 2895059. PMID 20534556.
Ahlert, J.; Shepard, E.; Lomovskaya, N.; Zazopoulos, E.; Staffa, A. (2002), "The calicheamicin gene cluster and its iterative type I enediyne", Science, 297 (5584): 1173–6, Bibcode:2002Sci...297.1173A, doi:10.1126/science.1072105, PMID 12183629, S2CID 8227050
Galm, U; Hager, MH; Van Lanen, SG; Ju, J; Thorson, JS; Shen, B (Feb 2005). "Antitumor antibiotics: bleomycin, enediynes, and mitomycin". Chemical Reviews. 105 (2): 739–58. doi:10.1021/cr030117g. PMID 15700963.
Zhang, C; Griffith, BR; Fu, Q; Albermann, C; Fu, X; Lee, IK; Li, L; Thorson, JS (Sep 1, 2006). "Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions". Science. 313 (5791): 1291–4. Bibcode:2006Sci...313.1291Z. doi:10.1126/science.1130028. PMID 16946071. S2CID 38072017.
Gantt, RW; Peltier-Pain, P; Cournoyer, WJ; Thorson, JS (Aug 21, 2011). "Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions". Nature Chemical Biology. 7 (10): 685–91. doi:10.1038/nchembio.638. PMC 3177962. PMID 21857660.
Chang, A.; Singh, S.; Helmich, K. (2011), "Complete set of glycosyltransferase structures in the calicheamicin biosynthetic pathway reveals the origin of regiospecificity", Proceedings of the National Academy of Sciences, 108 (43): 17649–54, Bibcode:2011PNAS..10817649C, doi:10.1073/pnas.1108484108, PMC 3203770, PMID 21987796
Biggins, JB; Onwueme, KC; Thorson, JS (Sep 12, 2003). "Resistance to enediyne antitumor antibiotics by CalC self-sacrifice". Science. 301 (5639): 1537–41. Bibcode:2003Sci...301.1537B. doi:10.1126/science.1086695. PMID 12970566. S2CID 45533019.
Singh, S; Hager, MH; Zhang, C; Griffith, BR; Lee, MS; Hallenga, K; Markley, JL; Thorson, JS (Aug 22, 2006). "Structural insight into the self-sacrifice mechanism of enediyne resistance". ACS Chemical Biology. 1 (7): 451–60. doi:10.1021/cb6002898. PMID 17168523.
Elshahawi, SI; Ramelot, TA; Seetharaman, J; Chen, J; Singh, S; Yang, Y; Pederson, K; Kharel, MK; Xiao, R; Lew, S; Yennamalli, RM; Miller, MD; Wang, F; Tong, L; Montelione, GT; Kennedy, MA; Bingman, CA; Zhu, H; Phillips GN, Jr; Thorson, JS (Aug 13, 2014). "Structure-Guided Functional Characterization of Enediyne Self-Sacrifice Resistance Proteins, CalU16 and CalU19". ACS Chemical Biology. 9 (10): 2347–58. doi:10.1021/cb500327m. PMC 4201346. PMID 25079510.

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S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC 49132. PMID 1584797.
Horsman, GP; Chen, Y; Thorson, JS; Shen, B (Jun 22, 2010). "Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes". Proc Natl Acad Sci U S A. 107 (25): 11331–5. Bibcode:2010PNAS..10711331H. doi:10.1073/pnas.1003442107. PMC 2895059. PMID 20534556.
Ahlert, J.; Shepard, E.; Lomovskaya, N.; Zazopoulos, E.; Staffa, A. (2002), "The calicheamicin gene cluster and its iterative type I enediyne", Science, 297 (5584): 1173–6, Bibcode:2002Sci...297.1173A, doi:10.1126/science.1072105, PMID 12183629, S2CID 8227050
Zhang, C; Griffith, BR; Fu, Q; Albermann, C; Fu, X; Lee, IK; Li, L; Thorson, JS (Sep 1, 2006). "Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions". Science. 313 (5791): 1291–4. Bibcode:2006Sci...313.1291Z. doi:10.1126/science.1130028. PMID 16946071. S2CID 38072017.
Chang, A.; Singh, S.; Helmich, K. (2011), "Complete set of glycosyltransferase structures in the calicheamicin biosynthetic pathway reveals the origin of regiospecificity", Proceedings of the National Academy of Sciences, 108 (43): 17649–54, Bibcode:2011PNAS..10817649C, doi:10.1073/pnas.1108484108, PMC 3203770, PMID 21987796
Biggins, JB; Onwueme, KC; Thorson, JS (Sep 12, 2003). "Resistance to enediyne antitumor antibiotics by CalC self-sacrifice". Science. 301 (5639): 1537–41. Bibcode:2003Sci...301.1537B. doi:10.1126/science.1086695. PMID 12970566. S2CID 45533019.

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Maiese, William M; Lechevalier, Mary P; Lechevalier, Hubert A; Korshalla, Joseph; Kuck, Nydia; Fantini, Amadeo; Wildey, Mary Jo; Thomas, John; Greenstein, Michael (April 1989). "Calicheamicins, a novel family of antitumor antibiotics: taxonomy, fermentation and biological properties". Journal of Antibiotics. 42 (4): 558–63. doi:10.7164/antibiotics.42.558. PMID 2722671.
Lee, May D.; Manning, Joann K.; Williams, David R.; Kuck, Nydia A.; Testa, Raymond T.; Borders, Donald B. (July 1989). "Calichemicins, a novel family of antitumor antibiotics. 3. Isolation, purification and characterization of calichemicins β1Br, γ1Br, α2I, α3I, β1I, γ1I, and Δ1I". Journal of Antibiotics. 42 (7): 1070–87. doi:10.7164/antibiotics.42.1070. PMID 2753814.
G.A. Ellestad (2011). "Structural and Conformational Features Relevant to the Anti-Tumor Activity of Calichemicin γ1I". Chirality. 23 (8): 660–671. doi:10.1002/chir.20990. PMID 21800378.
S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC 49132. PMID 1584797.
Simkhada D, Oh TJ, Kim EM, Yoo JC, Sohng JK (January 2009). "Cloning and characterization of CalS7 from Micromonospora echinospora sp. calichensis as a glucose-1-phosphate nucleotidyltransferase". Biotechnol. Lett. 31 (1): 147–53. doi:10.1007/s10529-008-9844-9. PMID 18807197. S2CID 2115227.
Zhang C, Bitto E, Goff RD, Singh S, Bingman CA, Griffith BR, Albermann C, Phillips GN Jr, Thorson JS (Aug 25, 2008). "Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis". Chem. Biol. 15 (8): 842–53. doi:10.1016/j.chembiol.2008.06.011. PMC 2965851. PMID 18721755.
Horsman, GP; Chen, Y; Thorson, JS; Shen, B (Jun 22, 2010). "Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes". Proc Natl Acad Sci U S A. 107 (25): 11331–5. Bibcode:2010PNAS..10711331H. doi:10.1073/pnas.1003442107. PMC 2895059. PMID 20534556.
Ahlert, J.; Shepard, E.; Lomovskaya, N.; Zazopoulos, E.; Staffa, A. (2002), "The calicheamicin gene cluster and its iterative type I enediyne", Science, 297 (5584): 1173–6, Bibcode:2002Sci...297.1173A, doi:10.1126/science.1072105, PMID 12183629, S2CID 8227050
Galm, U; Hager, MH; Van Lanen, SG; Ju, J; Thorson, JS; Shen, B (Feb 2005). "Antitumor antibiotics: bleomycin, enediynes, and mitomycin". Chemical Reviews. 105 (2): 739–58. doi:10.1021/cr030117g. PMID 15700963.
Zhang, C; Griffith, BR; Fu, Q; Albermann, C; Fu, X; Lee, IK; Li, L; Thorson, JS (Sep 1, 2006). "Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions". Science. 313 (5791): 1291–4. Bibcode:2006Sci...313.1291Z. doi:10.1126/science.1130028. PMID 16946071. S2CID 38072017.
Gantt, RW; Peltier-Pain, P; Cournoyer, WJ; Thorson, JS (Aug 21, 2011). "Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions". Nature Chemical Biology. 7 (10): 685–91. doi:10.1038/nchembio.638. PMC 3177962. PMID 21857660.
Chang, A.; Singh, S.; Helmich, K. (2011), "Complete set of glycosyltransferase structures in the calicheamicin biosynthetic pathway reveals the origin of regiospecificity", Proceedings of the National Academy of Sciences, 108 (43): 17649–54, Bibcode:2011PNAS..10817649C, doi:10.1073/pnas.1108484108, PMC 3203770, PMID 21987796
Biggins, JB; Onwueme, KC; Thorson, JS (Sep 12, 2003). "Resistance to enediyne antitumor antibiotics by CalC self-sacrifice". Science. 301 (5639): 1537–41. Bibcode:2003Sci...301.1537B. doi:10.1126/science.1086695. PMID 12970566. S2CID 45533019.
Singh, S; Hager, MH; Zhang, C; Griffith, BR; Lee, MS; Hallenga, K; Markley, JL; Thorson, JS (Aug 22, 2006). "Structural insight into the self-sacrifice mechanism of enediyne resistance". ACS Chemical Biology. 1 (7): 451–60. doi:10.1021/cb6002898. PMID 17168523.
Elshahawi, SI; Ramelot, TA; Seetharaman, J; Chen, J; Singh, S; Yang, Y; Pederson, K; Kharel, MK; Xiao, R; Lew, S; Yennamalli, RM; Miller, MD; Wang, F; Tong, L; Montelione, GT; Kennedy, MA; Bingman, CA; Zhu, H; Phillips GN, Jr; Thorson, JS (Aug 13, 2014). "Structure-Guided Functional Characterization of Enediyne Self-Sacrifice Resistance Proteins, CalU16 and CalU19". ACS Chemical Biology. 9 (10): 2347–58. doi:10.1021/cb500327m. PMC 4201346. PMID 25079510.

ncbi.nlm.nih.gov

S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC 49132. PMID 1584797.
Zhang C, Bitto E, Goff RD, Singh S, Bingman CA, Griffith BR, Albermann C, Phillips GN Jr, Thorson JS (Aug 25, 2008). "Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis". Chem. Biol. 15 (8): 842–53. doi:10.1016/j.chembiol.2008.06.011. PMC 2965851. PMID 18721755.
Horsman, GP; Chen, Y; Thorson, JS; Shen, B (Jun 22, 2010). "Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes". Proc Natl Acad Sci U S A. 107 (25): 11331–5. Bibcode:2010PNAS..10711331H. doi:10.1073/pnas.1003442107. PMC 2895059. PMID 20534556.
Gantt, RW; Peltier-Pain, P; Cournoyer, WJ; Thorson, JS (Aug 21, 2011). "Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions". Nature Chemical Biology. 7 (10): 685–91. doi:10.1038/nchembio.638. PMC 3177962. PMID 21857660.
Chang, A.; Singh, S.; Helmich, K. (2011), "Complete set of glycosyltransferase structures in the calicheamicin biosynthetic pathway reveals the origin of regiospecificity", Proceedings of the National Academy of Sciences, 108 (43): 17649–54, Bibcode:2011PNAS..10817649C, doi:10.1073/pnas.1108484108, PMC 3203770, PMID 21987796
Elshahawi, SI; Ramelot, TA; Seetharaman, J; Chen, J; Singh, S; Yang, Y; Pederson, K; Kharel, MK; Xiao, R; Lew, S; Yennamalli, RM; Miller, MD; Wang, F; Tong, L; Montelione, GT; Kennedy, MA; Bingman, CA; Zhu, H; Phillips GN, Jr; Thorson, JS (Aug 13, 2014). "Structure-Guided Functional Characterization of Enediyne Self-Sacrifice Resistance Proteins, CalU16 and CalU19". ACS Chemical Biology. 9 (10): 2347–58. doi:10.1021/cb500327m. PMC 4201346. PMID 25079510.

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Total Synthesis and the Creative Process: An Interview with K.C. Nicolaou, Scripps Research Institute

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Simkhada D, Oh TJ, Kim EM, Yoo JC, Sohng JK (January 2009). "Cloning and characterization of CalS7 from Micromonospora echinospora sp. calichensis as a glucose-1-phosphate nucleotidyltransferase". Biotechnol. Lett. 31 (1): 147–53. doi:10.1007/s10529-008-9844-9. PMID 18807197. S2CID 2115227.
Ahlert, J.; Shepard, E.; Lomovskaya, N.; Zazopoulos, E.; Staffa, A. (2002), "The calicheamicin gene cluster and its iterative type I enediyne", Science, 297 (5584): 1173–6, Bibcode:2002Sci...297.1173A, doi:10.1126/science.1072105, PMID 12183629, S2CID 8227050
Zhang, C; Griffith, BR; Fu, Q; Albermann, C; Fu, X; Lee, IK; Li, L; Thorson, JS (Sep 1, 2006). "Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions". Science. 313 (5791): 1291–4. Bibcode:2006Sci...313.1291Z. doi:10.1126/science.1130028. PMID 16946071. S2CID 38072017.
Biggins, JB; Onwueme, KC; Thorson, JS (Sep 12, 2003). "Resistance to enediyne antitumor antibiotics by CalC self-sacrifice". Science. 301 (5639): 1537–41. Bibcode:2003Sci...301.1537B. doi:10.1126/science.1086695. PMID 12970566. S2CID 45533019.

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Calicheamicin and Esperamicin are the two most potent antitumor agents known to man Archived 2008-09-21 at the Wayback Machine, Univ Of Georgia, Chem 4500

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Calicheamicin and Esperamicin are the two most potent antitumor agents known to man Archived 2008-09-21 at the Wayback Machine, Univ Of Georgia, Chem 4500

Calicheamicin (English Wikipedia)

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