The structures of novel nucleoside antibiotics, miharamycin A and miharamycin B

Seto, Haruo; Koyama, Masato; Ogino, Hiroko; Tsuruoka, Takashi; Inouye, Shigeharu; Ōtake, Noboru

doi:10.1016/s0040-4039(00)81775-x

Cited by 53 publications

(36 citation statements)

References 6 publications

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“…The assignment of the 1 H and 13 C NMR spectroscopic resonance signals collected for miharamycin A supported the structure proposed by Seto. [5] Moreover, three key features allowed the non-ambiguous deduction of an S configuration for C-6': a small J H5'H6' value (1.8 Hz, gauchetype major orientation), a large J H5'C7' value (> 8 Hz, antitype major orientation, C-7' being the carboxylic carbon atom) and the existence of a H-1'/H-2'' NOE (associated distance ca. 4 ).…”

Section: Resultsmentioning

confidence: 99%

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Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Marcelo

Jiménez‐Barbero

Marrot

et al. 2008

Chemistry A European J

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Section: Resultsmentioning

confidence: 99%

“…[5] Miharamycins were found to be made up of an unusual higher monosaccharide component, appended to an N-terminal amino acid residue at C-6', and a purine nucleobase connected at N 9 . However, the absolute configuration at C-6' for both antibiotics remains undetermined.…”

Section: Introductionmentioning

confidence: 99%

Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Marcelo

Jiménez‐Barbero

Marrot

et al. 2008

Chemistry A European J

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“…They are also important structural moieties present in many natural products (3)(4)(5)(6)(7)(8)(9) pyranoside sugar β-amino acid. The 6-deoxy-6-aminoheptopyranuronic acid moieties in amipurimycin (5) [32,33] and miharamycins (6) [34] are basically sugar α-amino acids. Nucleoside antifungal agent, polyoxin J (7) [35,36] and herbicide hydantocidin (8) [37,38] also contain sugar α-amino acids, the latter having an anomeric α-amino acid moiety.…”

Section: Natural Products Containing Sugar Amino Acidsmentioning

confidence: 99%

Sugar Amino Acids and Their Uses in Designing Bioactive Molecules

Chakraborty¹,

Ghosh²,

Jayaprakash

2002

CMC

111

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In search of new molecular entities for discovering new drugs and materials, organic chemists are looking for innovative approaches that try to imitate nature in assembling quickly large number of distinct and diverse molecular structures from 'nature-like' and yet unnatural designer building blocks using combinatorial approach. The main objective in developing such libraries is to mimic the diversities displayed in structures and properties of natural products. The unnatural building blocks used in these assemblies are carefully designed to manifest the structural diversities of the monomeric units used by nature like amino acids, carbohydrates and nucleosides to build its arsenal. Compounds made of such unnatural building blocks are also expected to be more stable toward proteolytic cleavage in physiological systems than their natural counterparts. Sugar amino acids constitute an important class of such polyfunctional scaffolds where the carboxyl, amino and hydroxyl termini provide an excellent opportunity to organic chemists to create structural diversities akin to nature's molecular arsenal. Recent advances in the area of combinatorial chemistry give an unprecedented technological support for rapid compilations of sugar amino acid-based libraries exploiting the diversities of carbohydrate molecules and well-developed solid-phase peptide synthesis methods. This review describes the development of sugar amino acids as a novel class of peptidomimetic building blocks and their applications in creating large number of structurally diverse peptide-based molecules many of which display interesting three-dimensional structures as well as useful biological properties.

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“…Notable among these are azadirachtin (Broughton, Ley, Slawin, Williams & Morgan, 1986;Ley, Santafianos, Blaney & Simmonds, 1987) and miharamycin A and B (Seto et al, 1983); azadirachtin is an insect anti-feedant (Rembold, 1984;Koul, 1984a,b) and miharamycin A and B are active against the rice blast disease caused by Pyricularia oryzae (Seto et al, 1983). As a result of increasing interest in using simple sugars as chiral synthons, we are pursuing the search for convenient and efficient approaches to the synthesis of furopyran and related fused-ring systems from readily available sugars and their derivatives.…”

Section: Commentmentioning

confidence: 99%