Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium

Jioji Natadra Tabudravu; L. A. Morris; J. J. Kettenes-van den Bosch; Marcel Jaspars

doi:10.1016/S0040-4020(02)00898-0

Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium

Jioji Natadra Tabudravu, L. A. Morris, J. J. Kettenes-van den Bosch, Marcel Jaspars

Chemistry

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

The structure of a new cyclic octapeptide, axinellin C, (cyclo[Thr(1)-Val(2)-Pro(3)-Trp(4)-Pro(5)-Phe(6)-Pro(7)-Leu(8)]), with all-trans peptide bond geometry, was elucidated by a combination of 2D NMR methods and tandem mass spectrometry. The solution state conformation was determined by ROE restrained molecular dynamics calculations. The structural features were found to be similar to those of the crystal structure of the cyclic decapeptide, phakellistatin 8, despite differing peptide sequences. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	7863-7868
Number of pages	5
Journal	Tetrahedron
Volume	58
DOIs	https://doi.org/10.1016/S0040-4020(02)00898-0
Publication status	Published - 2002

Keywords

natural products
amino acids
peptides
Stylotella aurantium
sponge
nuclear magnetic resonance
mass spectrometry
restrained molecular dynamics
solution conformation
ASCIDIAN LISSOCLINUM-PATELLA
ANTINEOPLASTIC AGENTS
CONFORMATION
GROWTH
PHAKELLISTATIN-8
CYCLOPEPTIDES
ANTAMANIDE
CARTERI

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0040-4020(02)00898-0

Cite this

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title = "Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium",

abstract = "The structure of a new cyclic octapeptide, axinellin C, (cyclo[Thr(1)-Val(2)-Pro(3)-Trp(4)-Pro(5)-Phe(6)-Pro(7)-Leu(8)]), with all-trans peptide bond geometry, was elucidated by a combination of 2D NMR methods and tandem mass spectrometry. The solution state conformation was determined by ROE restrained molecular dynamics calculations. The structural features were found to be similar to those of the crystal structure of the cyclic decapeptide, phakellistatin 8, despite differing peptide sequences. (C) 2002 Elsevier Science Ltd. All rights reserved.",

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author = "Tabudravu, {Jioji Natadra} and Morris, {L. A.} and {Kettenes-van den Bosch}, {J. J.} and Marcel Jaspars",

year = "2002",

doi = "10.1016/S0040-4020(02)00898-0",

language = "English",

volume = "58",

pages = "7863--7868",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

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TY - JOUR

T1 - Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium

AU - Tabudravu, Jioji Natadra

AU - Morris, L. A.

AU - Kettenes-van den Bosch, J. J.

AU - Jaspars, Marcel

PY - 2002

Y1 - 2002

N2 - The structure of a new cyclic octapeptide, axinellin C, (cyclo[Thr(1)-Val(2)-Pro(3)-Trp(4)-Pro(5)-Phe(6)-Pro(7)-Leu(8)]), with all-trans peptide bond geometry, was elucidated by a combination of 2D NMR methods and tandem mass spectrometry. The solution state conformation was determined by ROE restrained molecular dynamics calculations. The structural features were found to be similar to those of the crystal structure of the cyclic decapeptide, phakellistatin 8, despite differing peptide sequences. (C) 2002 Elsevier Science Ltd. All rights reserved.

AB - The structure of a new cyclic octapeptide, axinellin C, (cyclo[Thr(1)-Val(2)-Pro(3)-Trp(4)-Pro(5)-Phe(6)-Pro(7)-Leu(8)]), with all-trans peptide bond geometry, was elucidated by a combination of 2D NMR methods and tandem mass spectrometry. The solution state conformation was determined by ROE restrained molecular dynamics calculations. The structural features were found to be similar to those of the crystal structure of the cyclic decapeptide, phakellistatin 8, despite differing peptide sequences. (C) 2002 Elsevier Science Ltd. All rights reserved.

KW - natural products

KW - amino acids

KW - peptides

KW - Stylotella aurantium

KW - sponge

KW - nuclear magnetic resonance

KW - mass spectrometry

KW - restrained molecular dynamics

KW - solution conformation

KW - ASCIDIAN LISSOCLINUM-PATELLA

KW - ANTINEOPLASTIC AGENTS

KW - CONFORMATION

KW - GROWTH

KW - PHAKELLISTATIN-8

KW - CYCLOPEPTIDES

KW - ANTAMANIDE

KW - CARTERI

U2 - 10.1016/S0040-4020(02)00898-0

DO - 10.1016/S0040-4020(02)00898-0

M3 - Article

SN - 0040-4020

VL - 58

SP - 7863

EP - 7868

JO - Tetrahedron

JF - Tetrahedron

ER -

Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium

Abstract

Keywords

UN SDGs

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