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Solid-phase synthesis of cyclic peptide chitinase inhibitors

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Solid-phase synthesis of cyclic peptide chitinase inhibitors : SAR of the argifin scaffold. / Dixon, Mark J.; Nathubhai, Amit; Andersen, Ole A.; van Aalten, Daan M. F.; Eggleston, Ian M.

In: Organic and Biomolecular Chemistry, Vol. 7, No. 2, 2009, p. 259-268.

Research output: Contribution to journalArticle

Harvard

Dixon, MJ, Nathubhai, A, Andersen, OA, van Aalten, DMF & Eggleston, IM 2009, 'Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold' Organic and Biomolecular Chemistry, vol 7, no. 2, pp. 259-268.

APA

Dixon, M. J., Nathubhai, A., Andersen, O. A., van Aalten, D. M. F., & Eggleston, I. M. (2009). Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold. Organic and Biomolecular Chemistry, 7(2), 259-268doi: 10.1039/b815077j

Vancouver

Dixon MJ, Nathubhai A, Andersen OA, van Aalten DMF, Eggleston IM. Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold. Organic and Biomolecular Chemistry. 2009;7(2):259-268.

Author

Dixon, Mark J.; Nathubhai, Amit; Andersen, Ole A.; van Aalten, Daan M. F.; Eggleston, Ian M. / Solid-phase synthesis of cyclic peptide chitinase inhibitors : SAR of the argifin scaffold.

In: Organic and Biomolecular Chemistry, Vol. 7, No. 2, 2009, p. 259-268.

Research output: Contribution to journalArticle

Bibtex - Download

@article{a20e91c811b84f8ba5e4c35ca6df80f9,
title = "Solid-phase synthesis of cyclic peptide chitinase inhibitors",
author = "Dixon, {Mark J.} and Amit Nathubhai and Andersen, {Ole A.} and {van Aalten}, {Daan M. F.} and Eggleston, {Ian M.}",
year = "2009",
volume = "7",
number = "2",
pages = "259--268",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Solid-phase synthesis of cyclic peptide chitinase inhibitors

T2 - SAR of the argifin scaffold

A1 - Dixon,Mark J.

A1 - Nathubhai,Amit

A1 - Andersen,Ole A.

A1 - van Aalten,Daan M. F.

A1 - Eggleston,Ian M.

AU - Dixon,Mark J.

AU - Nathubhai,Amit

AU - Andersen,Ole A.

AU - van Aalten,Daan M. F.

AU - Eggleston,Ian M.

PY - 2009

Y1 - 2009

N2 - <p>A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the linear peptide chain by Fmoc SPPS prior to cyclisation and side-chain manipulation on-resin. Introduction of the key N-methyl carbamoyl-substituted Arg side chain is achieved via derivatisation of a selectively protected Orn residue, prior to cleavage from the resin and side-chain deprotection. A severe aspartimide side-reaction observed upon final deprotection is circumvented by the use of a novel aqueous acidolysis procedure. The. exibility of the synthesis is demonstrated by the preparation of a series of argifin analogues designed from the X-ray structure of the natural product in complex with a representative family 18 chitinase.</p>

AB - <p>A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the linear peptide chain by Fmoc SPPS prior to cyclisation and side-chain manipulation on-resin. Introduction of the key N-methyl carbamoyl-substituted Arg side chain is achieved via derivatisation of a selectively protected Orn residue, prior to cleavage from the resin and side-chain deprotection. A severe aspartimide side-reaction observed upon final deprotection is circumvented by the use of a novel aqueous acidolysis procedure. The. exibility of the synthesis is demonstrated by the preparation of a series of argifin analogues designed from the X-ray structure of the natural product in complex with a representative family 18 chitinase.</p>

KW - Acidic mammalian chitinase

KW - Butyloxycarbonyl group

KW - Efficient synthesis

KW - Product

KW - Chitotriosidase

KW - Removal

KW - Cell

KW - Parasite

KW - Collagen

KW - Analogs

U2 - 10.1039/b815077j

DO - 10.1039/b815077j

M1 - Article

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 2

VL - 7

SP - 259

EP - 268

ER -

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