Studies on the Total Synthesis of Bleomycin

Hecht, Sidney M.; Burlett, Donald J.; Mushika, Yoshitaka; Kuroda, Yasuhisa; Levin, Mark

doi:10.1007/978-1-4612-6191-9_4

Cited by 6 publications

(9 citation statements)

References 18 publications

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“…220–224 We developed a modular total synthesis of bleomycin A2 that permitted the total synthesis and examination of nearly 70 analogs of the natural product, 225–242 probing each subunit and substituent in the structure. 223 These studies confirmed the origin of DNA cleavage selectivity derived from G triplex-like H-bonding in the minor groove, 239 defined fundamental conformational properties of bleomycin that contribute to the efficiency of DNA cleavage, 240,241 clarified the functional roles of the individual subunits and their substituents, 223 and in collaboration with JoAnne Stubbe provided a NMR-derived high resolution structure of DNA bound deglycobleomycin A2.…”

Section: Introductionmentioning

confidence: 99%

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface

Boger

2017

J. Org. Chem.

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A Perspective of work in our laboratory on the examination of biologically active compounds, especially natural products, is presented. In the context of individual programs and along with a summary of our work, selected cases are presented that illustrate the impact single atom changes can have on the biological properties of the compounds. The examples were chosen to highlight single heavy atom changes that improve activity, rather than those that involve informative alterations that reduce or abolish activity. The examples were also chosen to illustrate that the impact of such single-atom changes can originate from steric, electronic, conformational, or H-bonding effects, from changes in functional reactivity, from fundamental intermolecular interactions with a biological target, from introduction of a new or altered functionalization site, or from features as simple as improvements in stability or physical properties. Nearly all the examples highlighted represent not only unusual instances of productive deep-seated natural product modifications and were introduced through total synthesis but are also remarkable in that they are derived from only a single heavy atom change in the structure.

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Section: Introductionmentioning

confidence: 99%

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface

Boger

2017

J. Org. Chem.

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“…The bleomycins are glycopeptide-derived antitumor antibiotics believed to exert their therapeutic effects via DNA degradation [ 1121 , 1217 ]. Bleomycin-mediated DNA degradation requires O 2 and a redox-active metal ion such as Fe, Cu, or Mn [ 1218 , 1219 ].…”

Section: Addendamentioning

confidence: 99%

New chemical and stereochemical applications of organoiron complexes

Fatiadi

1991

J. RES. NATL. INST. STAN.

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The objective of this review is to provide a current overview of the rapidly developing chemistry of organometallic complexes and particularly organoiron complexes useful in asymmetric and stereoselective reactions. Also covered are stereoselective reactions of α, β-unsaturated acyl ligands bound to the chiral auxiliary [(η5-C5H5) Fe(CO)(PPh3)] and new applications of organoiron complexes in the synthesis of natural products. The mechanistic aspects and stabilizing effects of the Fe(CO)3 group for alkenes or conjugated dienes are discussed. A brief summary of recent work on the special role of iron in biological reactions is also included.

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“…Bleomycins (BLMs) are well-known antibiotics related to the glycopeptide family with strong antitumor activity and are currently used clinically in the treatment of skin, head, neck, and testicular cancers [1][2][3]. The bithiazole moiety is one domain of bleomycin, which was shown to interact with DNA [4,5].…”

Section: Introductionmentioning

confidence: 99%

Cadmium(II) complexes containing 2,2′-dimethyl-4,4′-bithiazole ligand: synthesis, characterization, and crystal structure

Notash

Safari

Abedi

et al. 2009

Journal of Coordination Chemistry

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Mononuclear and coordination polymer compounds of 2,2 0 -dimethyl-4,4 0 -bithiazole (dm4bt) ligand have been prepared by metallation of dm4bt with Cd(NO 3 ) 2 Á 4H 2 O and CdCl 2 Á H 2 O. The compounds were characterized by IR, 1 H NMR, UV-Vis spectroscopy, and X-ray crystallography. The structural study of [Cd(dm4bt) 2 (NO 3 ) 2 ] Á H 2 O (1) shows that the complex is a monomeric seven-coordinate (CdN 4 O 3 ) cadmium(II)-bithiazole system with two bidentate dm4bt and mono and bidentate nitrates. The structure of [Cd(dm4bt)Cl 2 ] n (2) is a distorted octahedral environment around the cadmium(II) (CdN 2 Cl 4 ) forming a 1-D coordination polymer as a result of bridging by two chlorides and 2-D structure from -stacking interactions.

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Studies on the Total Synthesis of Bleomycin

Cited by 6 publications

References 18 publications

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface

New chemical and stereochemical applications of organoiron complexes

Cadmium(II) complexes containing 2,2′-dimethyl-4,4′-bithiazole ligand: synthesis, characterization, and crystal structure

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