N,N`-dissuccinimidyl carbonate: a useful reagent for alkoxycarbonylation of amines

Ghosh, Arun K.; Duong, Tien T.; Mckee, S. P.; Thompson, Wayne J.

doi:10.1016/s0040-4039(00)78856-3

Cited by 103 publications

(64 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 5 was converted into PCB-NHS ester 6 by using a modification of a procedure described previously (13). Compound 5 (1.07 g; 2 mmol) was dissolved in 10 ml of dimethylformamide.…”

mentioning

confidence: 99%

Photocleavable biotin derivatives: a versatile approach for the isolation of biomolecules.

Olejnik

Sonar²,

Krzymanska-Olejnik³

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

112

View full text Add to dashboard Cite

While the strong biotin-avidin interaction has been widely used for the detection of biomolecules, its irreversibility complicates their isolation. We report the synthesis of a photocleavable biotin derivative (PCB) which eliminates many limitations of existing methods. This reagent contains a biotin moiety linked through a spacer arm to a photocleavable moiety, which reacts selectively with primary amino groups on any substrate. In experiments using [leucine] -enkephalin as a model substrate, we show that PCB retains its high affinity toward avidin/streptavidin and allows rapid (<5 min) and efficient (>99%o) photorelease of the substrate in a completely unaltered form. Photocleavable biotins should be useful in numerous applications involving the isolation of proteins, nucleic acids, lipids, and cells.

show abstract

“…Compound 5 was converted into PCB-NHS ester 6 by using a modification of a procedure described previously (13). Compound 5 (1.07 g; 2 mmol) was dissolved in 10 ml of dimethylformamide.…”

mentioning

confidence: 99%

Photocleavable biotin derivatives: a versatile approach for the isolation of biomolecules.

Olejnik

Sonar²,

Krzymanska-Olejnik³

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

112

View full text Add to dashboard Cite

show abstract

“…6,7 The method whereby the chloroformate derivative of (S)-3-hydroxytetrahydrofuran is made by treating (S)-3-hydroxytetrahydrofuran with phosgene, followed by the addition of compound 2, did not yield the desired carbamoyl compound 3. The second approach, using (S)-3-tetrahydrofuranylsuccinimidyl carbonate, a reagent that other workers have employed to convert amines to carbamoyl products in good yields, 7,8 was smoothly executed. We made the reagent, 3-(S)-tetrahydrofuranylsuccinimidyl carbonate, from 3-(S)-hydroxytetrahydrofuran and N,N-disuccinimidyl carbonate, according to the method of Ghosh.…”

Section: Resultsmentioning

confidence: 99%

“…We made the reagent, 3-(S)-tetrahydrofuranylsuccinimidyl carbonate, from 3-(S)-hydroxytetrahydrofuran and N,N-disuccinimidyl carbonate, according to the method of Ghosh. 8 Compound 2 was reacted with 3-(S-)-tetrahydrofuranylsuccinimidyl carbonate in the presence of triethylamine, and the reaction afforded 3 in 87% yield.…”

Section: Resultsmentioning

confidence: 99%

“…To a stirred solution of 2 (1.82 g, 3.5 mmol) and triethylamine (906 ml, 6.47 mmol) in dichloromethane (15 ml) was added 3-(S)-tetrahydrofuranylsuccinimidyl carbonate 8 (840 mg, 3.66 mmol) in dry dichloromethane (8 ml). After 3 h at room temperature, the reaction mixture was diluted with dichloromethane (30 ml) and washed successively with aqueous NaHCO 3 (2 Â 20 ml), brine (30 ml) and dried on MgSO 4 .…”

Section: {3s-[(4-amino-benzenesulfonyl)-isobutylamino]-1smentioning

confidence: 99%

See 1 more Smart Citation

Isotope labeled ?HEA/HEE? moiety in the synthesis of labeled HIV-protease inhibitors?Part II

Ekhato

Liao

Plesescu

2005

J Label Compd Radiopharm

View full text Add to dashboard Cite

[2H5]‐Amprenavir and [2H 5]‐saquinavir have been prepared from a common labeled precursor (1S, 2S)‐(1‐oxiranyl‐2‐[2H5]phenylethyl)‐carbamic acid tert‐butyl ester, 1. Both of these compounds are in the ‘HEA’ class of HIV protease inhibitors. [2H5]‐Indinavir, a representative of the ‘HEE’ group of protease inhibitors, has also been synthesized. In the case of indinavir, 1S‐(2,2‐dimethyl‐8, 8a‐dihydro‐3aH‐indeno‐[1,2‐d]‐oxazol‐3R‐yl)‐2‐oxiranylmethyl‐3‐[2H5]phenylpropan‐1‐one, 11, provided the [phenyl‐2H5]‐HEE core structure for synthesis of the desired labeled compound. Copyright © 2005 John Wiley & Sons, Ltd.

show abstract

“…To achieve Dex immobilization, a peptide with the sequence GQPGK-furan was synthesized using standard Fmoc-mediated solid phase peptide synthesis methods as described previously [39,40]. The 3-furoic functionality was directly incorporated during the solid phase synthesis using a synthetic Fmoc protected amino acid analogue.…”

Section: Synthesis Of Furan-functionalized Dex Peptidementioning

confidence: 99%

Magnetic hyaluronic acid nanospheres via aqueous Diels–Alder chemistry to deliver dexamethasone for adipose tissue engineering

Yang

Fan

Chen

et al. 2015

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

N,N`-dissuccinimidyl carbonate: a useful reagent for alkoxycarbonylation of amines

Abstract: An efficient and mild method for alkoxycarbonylation of amines is described, utilizing commercially available N,N'-disuccinimidyl carbonate.

Cited by 103 publications

References 11 publications

Photocleavable biotin derivatives: a versatile approach for the isolation of biomolecules.

Photocleavable biotin derivatives: a versatile approach for the isolation of biomolecules.

Isotope labeled ?HEA/HEE? moiety in the synthesis of labeled HIV-protease inhibitors?Part II

Magnetic hyaluronic acid nanospheres via aqueous Diels–Alder chemistry to deliver dexamethasone for adipose tissue engineering

Contact Info

Product

Resources

About