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. 2012 Mar 5;51(10):2443-7.
doi: 10.1002/anie.201106325. Epub 2012 Jan 26.

Thiacycloalkynes for copper-free click chemistry

Gabriela de Almeida  1 , Ellen M Sletten, Hitomi Nakamura, Krishnan K Palaniappan, Carolyn R Bertozzi
Affiliations
Free PMC article

Thiacycloalkynes for copper-free click chemistry

Gabriela de Almeida et al. Angew Chem Int Ed Engl. .
Free PMC article
No abstract available

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Figures

Scheme 1
Scheme 1
Copper-free click-chemistry probes. a) Azide-labeled biomolecules can be selectively labeled with cyclooctyne reagents; b) an array of cyclooctynes for copper-free click chemistry; c) thiacycloalkynes reported herein.
Scheme 2
Scheme 2
Synthesis of thiaOCT. AIBN=2,2′-azobisisobutyronitrile, DMDO=2,2-dimethyldioxirane, HMDS=1,1,1,3,3,3-hexamethyldisilazide, LDA=lithium diisopropylamide, Piv=pivaloyl, Tf=trifluoromethylsulfonyl, THF=tetrahydrofuran, TIPS=triisopropylsilyl.
Scheme 3
Scheme 3
Retrosynthetic analysis of thiaalkynes 9 and 11.
Figure 1
Figure 1
Pretreatment of Ac4GalNAz-labeled cell lysates with TMTH (10) results in inhibition of phosphine–FLAG (PHOS–FLAG) labeling. Jurkat cells were incubated with Ac4GalNAz (50 μm) or vehicle (DMSO) for 3 days, and then lysed. a) The lysates were treated with TMTH (concentration 1 nm–1 mm) for 1.5 h followed by 500 μm phosphine–FLAG overnight; b) the lysates were analyzed by Western blot by using a primary anti-FLAG antibody and a secondary antibody conjugated to horseradish peroxidase. India Ink staining confirmed equal protein loading (see Figure S7 in the Supporting Information). DMSO=dimethyl sulfoxide.
Figure 2
Figure 2
TMTH selectively labels barstar containing azidohomoalanine (barstar-AHA). Barstar-AHA (b, d) or wildtype barstar (barstar-MET; a, c) in PBS was treated with TMTH (c, d) or vehicle (DMSO; a, b) for 120 h and then analyzed by mass spectrometry. Only barstar-AHA showed the expected mass shift of 168 Da. The mass shifts of 43 Da correspond to the N-terminal acylated barstar species.
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References

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