Peptide Coupling Reagents VI<sup>1</sup>. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)

Castro, Bertrand; Dormoy, Jean‐Robert; Dourtoglou, Basile; Evin, Geneviève; Selve, C.; Ziegler, Jean-Claude

doi:10.1055/s-1976-24189

Cited by 149 publications

(61 citation statements)

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“…The synthesis of compounds [20][21][22][23][24][25][26]28, and 29 will be described elsewhere (G.B.D., unpublished data). The peptide analogues (Table 2) were synthesized from compounds [19][20][21][22][23][24][25][26][27][28][29][30] tTo whom reprint requests should be addressed.…”

Section: Methodsmentioning

confidence: 99%

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Dreyer¹,

Metcalf²,

Tomaszek³

et al. 1989

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

193

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Inhibitors of the protease from human immunodeficiency virus 1 (HIV-1) were designed, synthesized, and kinetically characterized. Analogues of a heptapeptide substrate of HIV-1 protease with sequence similar to the pl7-p24 cleavage site in the natural substrate, Pr55519, were synthesized in which the scissile dipeptide bond was replaced with bonds from six categories of stable mimics of an aspartic proteolysis transition state or intermediate. These mimics included an analogue of statine, hydroxyethylene isosteres, two categories of phosphinic acids, a reduced amide isostere, and an a,a-difluoroketone. The resulting peptide analogues were linear competitive inhibitors of purified recombinant HIV-1 protease with inhibition constants ranging from 18 nM to 40 ,uM depending on the type of inhibitor. A truncated inhibitor, an analogue of a hexapeptide, retained full inhibitory potency. The most potent inhibitors, containing the hydroxyethylene isostere, effectively blocked the proteolytic processing of a recombinant form of Pr55s'9 by HIV-1 protease in a cell-free assay.

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Section: Methodsmentioning

confidence: 99%

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Dreyer¹,

Metcalf²,

Tomaszek³

et al. 1989

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

193

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“…The carboxyl group of (S)-2 was reduced by the treatment of its mixed anhydride with sodium borohydride [7] to give the alcohol (S)-3. After removal of the Boc groups by acidic treatment, two amino groups of (S)-4 were acylated with the benzylated 2,3-dihydroxybenzoic acid [8] using BOP reagent [9] …”

Section: Screening and Structure Determinationmentioning

confidence: 99%

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

et al. 2006

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In the screening of antitumor compounds from microbial secondary metabolites, myxochelin A was isolated from a culture broth of Nonomuraea pusilla TP-A0861. The absolute configuration was determined to be S by synthesizing both enantiomers from an L-or D-lysine derivative and comparing their specific rotations. Both enantiomers of myxochelin A showed remarkable inhibitory effects on the invasion of murine colon 26-L5 carcinoma cells at non-cytotoxic concentrations. Keywords myxochelin A, invasion, antitumor, Nonomuraea IntroductionTumor invasion is the major cause of treatment failure and death in cancer patients. The process of invasion into the basement membrane is a cascade of sequential complex steps, mainly consisting of tumor cell adhesion, enzymatic degradation of extracellular matrix proteins, and migration [1]. Compounds that inhibit any of these steps are expected to be candidates of anti-metastatic and/or anti-invasive agents. Hence, the clinical efficacy of such invasive inhibitors in cancer chemotherapy are extensively exploited [2,3].In the screening for anti-invasive compounds from natural products, myxochelin A (1) was found to inhibit the in vitro tumor cell invasion. Herein, we describe the isolation, structure determination, synthesis and biological properties of 1. Results and Discussion Screening and Structure DeterminationThe screening method employed in this study is based on the experimental model of tumor cell invasion using Transwell cell culture chamber and Matrigel, the reconstituted basement membrane [4]. This bioassay enables the detection of compounds that inhibit cell adhesion, enzymatic degradation of extracellular matrix, or migration. While screening for anti-invasive compounds from our natural products library, significant activity was shown by myxochelin A (1, Fig. 1

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“…Among the currently most popular peptide coupling reagents are the phosphonium [1,2] (BOP, PyBOP, etc.) and guanidinium [3] (HBTU, HATU, etc.)…”

mentioning

confidence: 99%

The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts

Carpino

Imazumi

El‐Faham

et al. 2002

Angewandte Chemie International Edition

208

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The strict exclusion of tertiary amines during the otherwise standard synthetic approach to the synthesis of the guanidinium‐type peptide coupling reagents HBTU (X = CH, see scheme) and HATU (X = N) allows the synthesis of the uronium‐type isomers of these guanidinium compounds, whose existence was until now pure speculation. These O isomers (O‐HBTU and O‐HATU) are more efficient coupling reagents than the N isomers.

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Peptide Coupling Reagents VI¹. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)

Cited by 149 publications

References 0 publications

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts

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Peptide Coupling Reagents VI1. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)

Cited by 149 publications

References 0 publications

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Inhibition of human immunodeficiency virus 1 protease in vitro: rational design of substrate analogue inhibitors.

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts

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Peptide Coupling Reagents VI¹. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)