Full Paper

Biphenomycin B and Derivatives: Total Synthesis and Translation Inhibition

  1. Dr. Yu-Peng He1,2,
  2. Hao Tan1,2,
  3. Dr. Lars Arve1,2,3,
  4. Dr. Sascha Baumann1,2,4,
  5. Prof. Dr. Herbert Waldmann1,2,*,
  6. Dr. Hans-Dieter Arndt1,2,5,*

Article first published online: 4 MAY 2011

DOI: 10.1002/asia.201000908

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 6, Issue 6, pages 1546–1556, June 6, 2011

Additional Information

How to Cite

He, Y.-P., Tan, H., Arve, L., Baumann, S., Waldmann, H. and Arndt, H.-D. (2011), Biphenomycin B and Derivatives: Total Synthesis and Translation Inhibition. Chem. Asian J., 6: 1546–1556. doi: 10.1002/asia.201000908

Author Information

  1. 1

    Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498

  2. 2

    Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)

  3. 3

    Current address: BayerCropScience GmbH, Alfred-Nobel-Straße 50, D-40789 Monheim (Germany)

  4. 4

    Current address: Stanford University School of Medicine, Department of Biochemistry, 279 Campus Drive, West Beckman Center, B469, Stanford, CA 94305-5307 (USA)

  5. 5

    New address: Friedrich-Schiller-Universität Jena, Lehrstuhl für Organische Chemie I, Humboldstrasse 10, D-07743 Jena (Germany)

*Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498

Publication History

  1. Issue published online: 27 MAY 2011
  2. Article first published online: 4 MAY 2011
  3. Manuscript Received: 17 DEC 2010

Funded by

  • Fonds der Chemischen Industrie

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Keywords:

  • antibiotics;
  • cross couplings;
  • natural products;
  • peptides;
  • synthesis design

Abstract

A full account on the synthesis of the antibiotic natural product biphenomycin B and several derivatives is reported, which employs a Suzuki coupling reaction of a free carboxylic acid and macrolactam formation as key transformations. Liberal exchange of the central amino acid was demonstrated. This procedure gave derivatives to study the influence of the polar side chain of the central amino acids on translation inhibition.

Featured Compounds

Compound 1
Molecular Weight:472.491
Molecular Formula:C23H28N4O7
InChIKey:Not Available
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Compound 2
Molecular Weight:488.4904
Molecular Formula:C23H28N4O8
InChIKey:Not Available
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Compound 3
Molecular Weight:731.7534
Molecular Formula:C32H45N9O11
InChIKey:Not Available
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4a
Molecular Weight:824.9594
Molecular Formula:C42H60N6O11
InChIKey:Not Available
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Compound 4b
Molecular Weight:869.957
Molecular Formula:C42H59N7O13
InChIKey:WFBZGMGSCAVZTQ-KUMHBBRUSA-N
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Compound 5
Molecular Weight:344.5251
Molecular Formula:C15H32N4O3Si
InChIKey:FTKCJQGBSAHMDE-NEPJUHHUSA-N
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Compound 6
Molecular Weight:636.6888
Molecular Formula:C34H40N2O10
InChIKey:Not Available
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Compound 7
Molecular Weight:455.2437
Molecular Formula:C18H18INO5
InChIKey:Not Available
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Compound 8
Molecular Weight:435.319
Molecular Formula:C22H34BNO7
InChIKey:Not Available
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Compound 9
Molecular Weight:321.1117
Molecular Formula:C10H12INO3
InChIKey:Not Available
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Compound 10
Molecular Weight:326.957
Molecular Formula:C8H8BrIO
InChIKey:Not Available
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Compound 12
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:Not Available
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Compound 13
Molecular Weight:262.0445
Molecular Formula:C8H7IO2
InChIKey:Not Available
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Compound 14
Molecular Weight:264.0603
Molecular Formula:C8H9IO2
InChIKey:Not Available
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Compound 9.HCl
Molecular Weight:357.573
Molecular Formula:C10H13ClINO3
InChIKey:NJEMVSDGMNYUQO-QRPNPIFTSA-N
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Compound 11
Molecular Weight:295.3755
Molecular Formula:C19H21NO2
InChIKey:Not Available
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Compound 15
Molecular Weight:371.599
Molecular Formula:C11H15ClINO3
InChIKey:Not Available
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Compound S,S-16
Molecular Weight:482.3121
Molecular Formula:C20H23IN2O4
InChIKey:Not Available
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Compound R,S-16
Molecular Weight:482.3121
Molecular Formula:C20H23IN2O4
InChIKey:Not Available
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Compound R,R-16
Molecular Weight:482.3121
Molecular Formula:C20H23IN2O4
InChIKey:Not Available
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Compound S,R-16
Molecular Weight:482.3121
Molecular Formula:C20H23IN2O4
InChIKey:Not Available
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Compound 17
Molecular Weight:421.2275
Molecular Formula:C15H20INO5
InChIKey:Not Available
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Compound 18
Molecular Weight:435.2541
Molecular Formula:C16H22INO5
InChIKey:Not Available
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Compound 19
Molecular Weight:231.2457
Molecular Formula:C10H17NO5
InChIKey:Not Available
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Compound 20
Molecular Weight:401.6129
Molecular Formula:C20H39NO5Si
InChIKey:Not Available
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Compound 21
Molecular Weight:415.5964
Molecular Formula:C20H37NO6Si
InChIKey:Not Available
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Compound 22
Molecular Weight:419.6281
Molecular Formula:C20H41NO6Si
InChIKey:Not Available
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Compound 23
Molecular Weight:444.6409
Molecular Formula:C20H40N4O5Si
InChIKey:ZTGHBCLGLUZYPE-CABCVRRESA-N
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Compound 24
Molecular Weight:963.1986
Molecular Formula:C49H70N6O12Si
InChIKey:JFFWAYHWMAMFGJ-QRIZJJBVSA-N
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Compound 25
Molecular Weight:788.9612
Molecular Formula:C40H52N6O9Si
InChIKey:OHUICKBQLALQEP-GJBCSVNNSA-N
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Compound 26
Molecular Weight:763.873
Molecular Formula:C41H53N3O11
InChIKey:Not Available
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Compound 27
Molecular Weight:835.9787
Molecular Formula:C45H61N3O12
InChIKey:Not Available
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Compound 28
Molecular Weight:941.0729
Molecular Formula:C51H64N4O13
InChIKey:Not Available
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Compound 30
Molecular Weight:605.635
Molecular Formula:C32H35N3O9
InChIKey:Not Available
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Compound 31
Molecular Weight:766.8354
Molecular Formula:C42H46N4O10
InChIKey:Not Available
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Compound 32
Molecular Weight:413.4238
Molecular Formula:C21H23N3O6
InChIKey:Not Available
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Compound 33
Molecular Weight:429.4232
Molecular Formula:C21H23N3O7
InChIKey:Not Available
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Compound 34
Molecular Weight:456.4916
Molecular Formula:C23H28N4O6
InChIKey:Not Available
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