Isolation and synthesis of 4-bromopyrrole-2-carboxyarginine and 4-bromopyrrole-2-carboxy-N(epsilon)-lysine from the marine sponge Stylissa caribica

Achim Grube; Ellen Lichte; Matthias Köck

doi:10.1021/np0502746

Isolation and synthesis of 4-bromopyrrole-2-carboxyarginine and 4-bromopyrrole-2-carboxy-N(epsilon)-lysine from the marine sponge Stylissa caribica

J Nat Prod. 2006 Jan;69(1):125-7. doi: 10.1021/np0502746.

Authors

Achim Grube¹, Ellen Lichte, Matthias Köck

Affiliation

¹ Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, D-27570 Bremerhaven, Germany.

PMID: 16441082
DOI: 10.1021/np0502746

Abstract

Two new bromopyrrole alkaloids were isolated from the Caribbean sponge Stylissa caribica. The new natural products, 4-bromopyrrole-2-carboxyarginine (1) and 4-bromopyrrole-2-carboxy-N(epsilon)-lysine (2), are derivatives of amino acids linked with a 4-bromopyrrole-2-carboxylic acid. The structures were elucidated on the basis of NMR and MS/MS data and their absolute configurations assigned via synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Animals
Arginine / analogs & derivatives
Arginine / chemical synthesis*
Arginine / isolation & purification*
Caribbean Region
Lysine / analogs & derivatives
Lysine / chemical synthesis*
Lysine / isolation & purification*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Porifera / chemistry*
Pyrroles

Substances

4-bromopyrrole-2-carboxy-N(epsilon)lysine
4-bromopyrrole-2-carboxyarginine
Alkaloids
Pyrroles
Arginine
Lysine