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Review
. 2011 Oct 12;111(10):6341-58.
doi: 10.1021/cr2001977. Epub 2011 Sep 16.

Exploring protein lipidation with chemical biology

Howard C Hang  1 , Maurine E Linder
Affiliations
Review

Exploring protein lipidation with chemical biology

Howard C Hang et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

FIGURE 1
FIGURE 1
Survey of cytosolic protein lipidation in eukaryotes. A) S-Farnesylation. B) S-Geranylgeranylation. C) C-phosphatidylethanolaminylation. D) N-myristoylation. E) N-palmitoylation. F) S-palmitoylation.
FIGURE 2
FIGURE 2
Schematic of maleimidocaproyl (MIC)-controlled ligation of S-farnesylated peptide to Ras GTPases or GFP.
FIGURE 3
FIGURE 3
Schematic of expressed protein ligation of Rab7 ligation to a fluorescent digeranylgeranylated hexapeptide. Chitin binding domain (CBD). * represents a dansyl group. Geranylgeranyl group (GG).
FIGURE 4
FIGURE 4
Schematics of lipopeptides used in EPL to generate lipidated semisynthetic proteins. A) Mono- and digeranylgeranylated peptides. B) S-farnesylated peptides modified with a cleavable thioester-linked palmitate (left) or noncleavable thioether-linked hexadecanoate (right) for maleimidocaproyl (MIC) ligation. C) Cys-Ser-Cys peptide modified with farnesyl-NBD (nitrobenzoxadiazole).
FIGURE 5
FIGURE 5
Model of the membrane association and GTPase cycles of Rab proteins.
FIGURE 6
FIGURE 6
Inhibitors of protein palmitoylation (A–D) and depalmitoylation (E). A) 2-bromopalmitate. B) Tunicamycin. C) Cerulenin. D) Compound V, 2-(2-hydroxy-5-nitro-benzylidene)-benzo[b]thiophen-3-one. E) Palmostatin B.
FIGURE 7
FIGURE 7
Model of Acylation-dependent Ras Trafficking. Endoplasmic reticulum (ER). Acylprotein thioesterase 1(APT1).
FIGURE 8
FIGURE 8
Reagents for chemical or enzymatic analysis of protein lipidation. A) NBD-farnesylpyrophosphate. B) Biotin-geranylpyrophosphate. A) HPDP-Biotin for ABE analysis of S-acylation.
FIGURE 9
FIGURE 9
Enrichment protocols for S-acylated proteins. A) Acyl-biotin exchange (ABE) with HPDP. B) Acyl-resin assisted capture (Acyl-RAC) with thiopropyl (TP)-sepharose. β-mercaptoethanol (β-ME). Dithiothreitol (DTT). Methylmethanethiosulfonate (MMTS). Tris(2-carboxyethyl)phosphine (TCEP).
FIGURE 10
FIGURE 10
Schematic for bioorthogonal detection and enrichment of lipidated proteins using alkynyl chemical reporters and CuAAC.
FIGURE 11
FIGURE 11
Bioorthogonal chemical reporters for analysis of lipid-modified proteins. A) Alkynyl-isoprenoid reporter. B). Alkynyl-fatty acid reporters. C) HDYOA reporter. D) Azido cholesteroylation reporter. E) Propargylcholine reporter.
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