Thiazole and oxazole peptides: biosynthesis and molecular machinery

Roy, Ranabir Sinha; Gehring, Amy M.; Milne, Jill C.; Belshaw, Peter J.; Walsh, Christopher T.

doi:10.1039/a806930a

Cited by 286 publications

(212 citation statements)

References 95 publications

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“…In the case of 7e (R 1 = H), the use of the Dess-Martin reagent appeared to be more fruitful than the Swern oxidation (35% vs. 5% yield of 9e by 1 H NMR). Unfortunately, the It was shown that the storage stability of products 9a-e is strongly affected by the steric volume of the substituent R 1 . In particular, the product 9a has limited stability in CH 2 Cl 2 solution (ca.…”

Section: Resultsmentioning

confidence: 99%

“…To analyze the optical purity of the products, compound 4a · 2HCl was derivatized with the Mosher's reagent, which gave a single diastereomer according to 1 H NMR and 19 F NMR analyses. In addition, the enantiomer of compound 11c was synthesized from D-N-Bocproline and used as a control for chiral stationary phase high-performance liquid chromatography (HPLC).…”

Section: Resultsmentioning

confidence: 99%

“…Since their isolation from marine products in the late 1980s, oxazole-containing peptidomimetics have been studied extensively by synthetic organic and medicinal chemists [1][2][3][4][5]. It is believed that many of these natural products are derived from enzymatic post-translational modifications of peptide-based precursors containing serine or threonine moieties [2].…”

Section: Introductionmentioning

confidence: 99%

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A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

Slobodyanyuk

Artamonov

Kulik

et al. 2018

Heterocyclic Communications

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A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazolecontaining peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides -aldehyde intermediates which demonstrate low to moderate stability -under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17-51% overall yield and has been used at up to a 45-g scale.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

Slobodyanyuk

Artamonov

Kulik

et al. 2018

Heterocyclic Communications

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“…This motif is biosynthesized from peptides whereby the amide carbonyl function of cysteine undergoes nucleophilic attack by its thiol tether, followed by dehydration. 20 Interestingly, traditional preparation methods of thiazolines could not biomimic its synthesis. However, Kelly et al…”

Section: 29mentioning

confidence: 99%

The Hendrickson ‘POP’ reagent and analogues thereof: synthesis, structure, and application in organic synthesis

Moussa¹

2012

Arkivoc

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This comprehensive review discusses the synthesis, structure, and application of the Hendrickson 'POP' reagent and its analogues in organic synthesis. Specifically, the review describes applications of the preceding dehydrating agents in functional group interconversions, heterocycle synthesis, and total synthesis of natural products. Many examples are provided from the literature to show the scope and selectivity (regio and chemo) in these transformations.

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“…In the present study, we aim to target these vectors, while introducing heterocycles, namely, oxazole or thiazole rings at the C-2 position in place of the amide linkage in our lead scaffold represented by SSA ( Figure 1) in order to probe rigidification at the amide linkage. Thiazoles and oxazoles are common structural features of many biologically important natural products and are typically used as isosteric replacements for the amide linkage in medicinal chemistry [36][37][38][39]. These heterocyclic rings increase the rigidity of the molecule and may potentially alter binding potency by reducing mobility around the amide group.…”

Section: Aimmentioning

confidence: 99%

Oxazole and Thiazole Analogs of Sulindac for Cancer Prevention

et al. 2018

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Aim:Experimental and epidemiological studies and clinical trials suggest that nonsteroidal antiinflammatory drugs possess antitumor potential. Sulindac, a widely used nonsteroidal anti-inflammatory drug, can prevent adenomatous colorectal polyps and colon cancer, especially in patients with familial adenomatous polyposis. Sulindac sulfide amide (SSA) is an amide-linked sulindac sulfide analog that showed in vivo antitumor activity in a human colon tumor xenograft model. Results/methodology: A new analog series with heterocyclic rings such as oxazole or thiazole at the C-2 position of sulindac was prepared and screened against prostate, colon and breast cancer cell lines to probe the effect of these novel substitutions on the activity of sulindac analogs. Conclusion: In general, replacement of the amide function of SSA analogs had a negative impact on the cell lines tested. A small number of hits incorporating rigid oxazole or thiazole groups in the sulindac scaffold in place of the amide linkage show comparable activity to our lead agent SSA. Graphical abstract:

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Thiazole and oxazole peptides: biosynthesis and molecular machinery

Cited by 286 publications

References 95 publications

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

The Hendrickson ‘POP’ reagent and analogues thereof: synthesis, structure, and application in organic synthesis

Oxazole and Thiazole Analogs of Sulindac for Cancer Prevention

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