Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity

Klemens Stratmann; David L. Burgoyne; Richard E. Moore; Gregory M.L. Patterson; Charles D. Smith

doi:10.1021/jo00103a011

Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity

Klemens Stratmann, David L. Burgoyne, Richard E. Moore, Gregory M.L. Patterson, Charles D. Smith

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Abstract

Hapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. & G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4S,8S,9S,12S)-9-benzyl-4-heptyl-8-hydroxy-12-isopropyl-3,10-dimethyl-1,5-dioxa-10-azacyclododecane-2,6,11 -trione by a combination of spectroscopic and chemical methods. The carbon skeleton of 2 was determined by two-dimensional ¹H— and ¹H—¹³C NMR correlation experiments and confirmed by mass spectral analysis. The relative and absolute stereochemistry was determined by coupling constant data and Mosher analysis of 2 and three degradation products obtained from acid hydrolysis of 2.

Original language	English (US)
Pages (from-to)	7219-7226
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	59
Issue number	24
DOIs	https://doi.org/10.1021/jo00103a011
State	Published - Dec 1 1994

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00103a011

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title = "Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity",

abstract = "Hapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. & G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4S,8S,9S,12S)-9-benzyl-4-heptyl-8-hydroxy-12-isopropyl-3,10-dimethyl-1,5-dioxa-10-azacyclododecane-2,6,11 -trione by a combination of spectroscopic and chemical methods. The carbon skeleton of 2 was determined by two-dimensional 1H— and 1H—13C NMR correlation experiments and confirmed by mass spectral analysis. The relative and absolute stereochemistry was determined by coupling constant data and Mosher analysis of 2 and three degradation products obtained from acid hydrolysis of 2.",

author = "Klemens Stratmann and Burgoyne, {David L.} and Moore, {Richard E.} and Patterson, {Gregory M.L.} and Smith, {Charles D.}",

year = "1994",

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doi = "10.1021/jo00103a011",

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journal = "Journal of Organic Chemistry",

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T1 - Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity

AU - Stratmann, Klemens

AU - Burgoyne, David L.

AU - Moore, Richard E.

AU - Patterson, Gregory M.L.

AU - Smith, Charles D.

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Hapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. & G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4S,8S,9S,12S)-9-benzyl-4-heptyl-8-hydroxy-12-isopropyl-3,10-dimethyl-1,5-dioxa-10-azacyclododecane-2,6,11 -trione by a combination of spectroscopic and chemical methods. The carbon skeleton of 2 was determined by two-dimensional 1H— and 1H—13C NMR correlation experiments and confirmed by mass spectral analysis. The relative and absolute stereochemistry was determined by coupling constant data and Mosher analysis of 2 and three degradation products obtained from acid hydrolysis of 2.

AB - Hapalosin (2), a novel cyclic depsipeptide from the blue-green alga (cyanobacterium) Hapalosiphon welwitschii W. & G. S. West (Stigonemataceae), shows MDR-reversing activity. Its structure has been determined to be (3S,4S,8S,9S,12S)-9-benzyl-4-heptyl-8-hydroxy-12-isopropyl-3,10-dimethyl-1,5-dioxa-10-azacyclododecane-2,6,11 -trione by a combination of spectroscopic and chemical methods. The carbon skeleton of 2 was determined by two-dimensional 1H— and 1H—13C NMR correlation experiments and confirmed by mass spectral analysis. The relative and absolute stereochemistry was determined by coupling constant data and Mosher analysis of 2 and three degradation products obtained from acid hydrolysis of 2.

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ER -

Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity

Abstract

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