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. 2006 Jan 5;8(1):131-4.
doi: 10.1021/ol052623t.

An alpha-formylglycine building block for fmoc-based solid-phase peptide synthesis

Jason Rush  1 , Carolyn R Bertozzi
Affiliations

An alpha-formylglycine building block for fmoc-based solid-phase peptide synthesis

Jason Rush et al. Org Lett. .

Abstract

[reaction: see text] Nearly all known sulfatases share a common active site modification that is required for their activity: conversion of cysteine to alpha-formylglycine. We report the synthesis of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis. The building block was incorporated into a synthetic peptide derived from the active site of a Mycobacterium tuberculosis sulfatase.

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Figures

Figure 1
Figure 1
Catalytic cycle of sulfatases.
Figure 2
Figure 2
Modified tripeptide 10.
Figure 3
Figure 3
Proposed mechanism for the formation of byproduct.
Figure 4
Figure 4
HPLC and mass spectrometry analysis of 9.
Figure 5
Figure 5
Mass spectrometry analysis of peptide 9 and its oxime adduct 15.
Scheme 1
Scheme 1
Synthesis of Fmoc-FGly Building-Block 8
See this image and copyright information in PMC

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