Peptide analogs containing the pentacyclo[5,4,0,02,6,03,6,05,9]undecane scaffold: conformational analysis in solution

Axt, Mariane; Oulyadi, Hassan; Pannecoucke, Xavier; Quirion, J.‐C.; Pohlmann, Adriana Raffin; Costa, Valentim Emı́lio Uberti

doi:10.1016/j.molstruc.2003.10.018

Cited by 2 publications

(2 citation statements)

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“…An expedient way to construct cage compounds makes use of an initial Diels–Alder reaction of a para -quinone with a cyclopentadiene followed by an intramolecular [2 + 2] photocycloaddition (Scheme ). − …”

Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…A nonrelated experimental and computational investigation on peptide analogues containing a PCU scaffold was recently published. 20 Consequently, a similar investigation on the trishomocubane peptide (Ac-Tris-NHMe; 3b) was performed and the results are compared herein with those previously obtained for the PCU cage peptide (4b). Trishomocubane is a chiral molecule with an unusual symmetry (Figure 1).…”

Section: Introductionmentioning

confidence: 96%

Analysis of the conformational profile of trishomocubane amino acid dipeptide

Bisetty¹,

Govender²,

Kruger³

2005

Biopolymers

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4-Amino-(D3)-trishomocubane-4-carboxylic acid is a constrained alpha-amino acid residue that exhibits promising conformational characteristics, i.e., helical and beta-turns. As part of the development of conformational guidelines for the design of peptides and protein surrogates, the conformational energy calculations on trishomocubane using molecular mechanics and ab initio methods are presented. The C(alpha) carbon of trishomocubane forms part of the cyclic structure, and consequently a peptidic environment was simulated with an acetyl group on its N-terminus and a methylamide group on its C-terminus. Ramachandran maps computed at the molecular mechanics level using the standard AMBER (parm94) force field libraries compared reasonably well with the corresponding maps computed at the Hartree Fock level, using the 6-31G* basis set. Trishomocubane peptide (Ac-Tris-NHMe) is characterized by four low energy conformers corresponding to the C7ax, C7eq, 3(10), and alpha(L) helical structures.

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Peptide analogs containing the pentacyclo[5,4,0,02,6,03,6,05,9]undecane scaffold: conformational analysis in solution

Cited by 2 publications

References 42 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Analysis of the conformational profile of trishomocubane amino acid dipeptide

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Peptide analogs containing the pentacyclo[5,4,0,02,6,03,6,05,9]undecane scaffold: conformational analysis in solution

Cited by 2 publications

References 42 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Analysis of the conformational profile of trishomocubane amino acid dipeptide

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions