Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns

Baravkar, Sachin B.; Wagh, Mahendra A.; Paul, Debasish; Santra, Manas Kumar; Sanjayan, Gangadhar J.

doi:10.1016/j.tetlet.2018.08.016

Cited by 2 publications

(2 citation statements)

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“…With standard peptide coupling reagents such as HBTU or PyBOP, the reaction proceeded with a low yield (less than 20 %). A segment doubling strategy to yield the tetrapeptide from corresponding dimer amine and dimer acid was not successful due to the commonly encountered cyclization observed with anthranilic acids [37] . Therefore, to synthesize tetrapeptide, the acid was first converted to benzoxazinone using EDCI, and ring opening was done with DBU in presence of dimer amine [38] .…”

Section: Resultsmentioning

confidence: 99%

“…A segment doubling strategy to yield the tetrapeptide from corresponding dimer amine and dimer acid was not successful due to the commonly encountered cyclization observed with anthranilic acids. [37] Therefore, to synthesize tetrapeptide, the acid was first converted to benzoxazinone using EDCI, and ring opening was done with DBU in presence of dimer amine. [38] Similarly, the tripeptides Boc-Pro-(3-FAnt)-Pro-OMe (3) and Boc-Pro-(6-FAnt)-Pro-OMe (7) were synthesized from corresponding benzoxazinone derivative and proline methyl ester.…”

Section: Synthesismentioning

confidence: 99%

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“Fluorine Effects” in Conformational Orchestration of α/β Hybrid Peptide with a 9‐membered Pseudo β‐Turn Motif

Patel,

Karmakar,

Tothadi

et al. 2024

Chemistry A European J

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Fluorine, the tiny robust atom, with its unique features has captured the attention of scientists in recent times, especially in drug discovery with its integration in small molecules, peptides, and proteins. However, studies to understand the ‘fluorine effects’ (‘fluorine magic’) on the conformation of molecules that follow ‘beyond the rule of 5’ are in the infancy yet significant in molecular design and function. For the first time, using short hybrid peptide sequence as an appropriate model, we examined the substitution effect (size, stereoelectronic effect, and hydrogen bonding) using X‐ray diffraction 2D‐NMR, and CD studies. The comparative study on their folding patterns with hydrogen‐substituted analogs can provide valuable insights into ‘flustrates’ fluorinated substrates’ design.

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Section: Resultsmentioning

confidence: 99%