Solid-phase synthesis of succinylhydroxamate peptides: Functionalized matrix metalloproteinase inhibitors

M.A. Leeuwenburgh; P.P. Geurink; T Klein; H.F Kauffman; G.A. van der Marel; Rainer Bischoff; H.S. Overkleeft

doi:10.1021/ol060409e

Solid-phase synthesis of succinylhydroxamate peptides: Functionalized matrix metalloproteinase inhibitors

M.A. Leeuwenburgh
, P.P. Geurink
, T Klein
, H.F Kauffman
, G.A. van der Marel
, Rainer Bischoff
, H.S. Overkleeft

Research output: Contribution to journal › Letter (Research letter) › Academic › peer-review

25 Citations (Scopus)

Abstract

A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.

Original language	English
Pages (from-to)	1705-1708
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	8
DOIs	https://doi.org/10.1021/ol060409e
Publication status	Published - 13-Apr-2006

Keywords

HYDROXAMIC ACIDS
DERIVATIVES
PROBES
RESIN

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Solid-phase synthesis of succinylhydroxamate peptides Functionalized
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title = "Solid-phase synthesis of succinylhydroxamate peptides: Functionalized matrix metalloproteinase inhibitors",

abstract = "A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.",

keywords = "HYDROXAMIC ACIDS, DERIVATIVES, PROBES, RESIN",

author = "M.A. Leeuwenburgh and P.P. Geurink and T Klein and H.F Kauffman and \{van der Marel\}, G.A. and Rainer Bischoff and H.S. Overkleeft",

note = "Department of Bio-organic Synthesis, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands, GUIDE Office, University Medical Center Groningen, 9713 AV, Groningen, The Netherlands, and Department of Analytical Biochemistry, Groningen University, PO Box 196, 9700 AD Groningen, The Netherlands",

year = "2006",

month = apr,

day = "13",

doi = "10.1021/ol060409e",

language = "English",

volume = "8",

pages = "1705--1708",

journal = "Organic letters",

issn = "1523-7052",

publisher = "AMER CHEMICAL SOC INC",

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TY - JOUR

T1 - Solid-phase synthesis of succinylhydroxamate peptides

T2 - Functionalized matrix metalloproteinase inhibitors

AU - Leeuwenburgh, M.A.

AU - Geurink, P.P.

AU - Klein, T

AU - Kauffman, H.F

AU - van der Marel, G.A.

AU - Bischoff, Rainer

AU - Overkleeft, H.S.

N1 - Department of Bio-organic Synthesis, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands, GUIDE Office, University Medical Center Groningen, 9713 AV, Groningen, The Netherlands, and Department of Analytical Biochemistry, Groningen University, PO Box 196, 9700 AD Groningen, The Netherlands

PY - 2006/4/13

Y1 - 2006/4/13

N2 - A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.

AB - A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.

KW - HYDROXAMIC ACIDS

KW - DERIVATIVES

KW - PROBES

KW - RESIN

U2 - 10.1021/ol060409e

DO - 10.1021/ol060409e

M3 - Letter (Research letter)

SN - 1523-7052

VL - 8

SP - 1705

EP - 1708

JO - Organic letters

JF - Organic letters

IS - 8

ER -

Solid-phase synthesis of succinylhydroxamate peptides: Functionalized matrix metalloproteinase inhibitors

Abstract

Keywords

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