Spatially close porphyrin pair linked by the cyclic peptide Gramicidin S

Arai, T.; Maruo, Naoki; Sumida, Yuko; Korosue, Chie; Nishino, Norikazu

doi:10.1039/a902774b

Cited by 11 publications

(11 citation statements)

References 11 publications

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“…The CD originating from the interaction of porphyrins and metalloporphyrins with polypeptides, proteins, [14][15][16][17][18][19][20][21] and nucleic acids [21][22][23][24][25] is beyond the scope of this survey. The CD originating from the interaction of porphyrins and metalloporphyrins with polypeptides, proteins, [14][15][16][17][18][19][20][21] and nucleic acids [21][22][23][24][25] is beyond the scope of this survey.…”

Section: Uv-vis Spectra Of Porphyrins and Metalloporphyrinsmentioning

confidence: 99%

“…The following discussion on the CD of porphyrins is divided into two sections: 1) CD of monoporphyrins, including induced CD (ICD) due to perturbation of the porphyrin Soret band by chiral substituents or ligands and CD of intrinsically chiral porphyrins; and 2) CD of interacting porphyrins arising from a through-space exciton coupling interaction. The CD originating from the interaction of porphyrins and metalloporphyrins with polypeptides, proteins, [14][15][16][17][18][19][20][21] and nucleic acids [21][22][23][24][25] is beyond the scope of this survey.…”

Section: Uv-vis Spectra Of Porphyrins and Metalloporphyrinsmentioning

confidence: 99%

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Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies

2000

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During the last few years, porphyrins and metalloporphyrins have attracted widespread attention as chromophores for studies in circular dichroism (CD), an indispensable chiroptical tool for monitoring chiral interactions. This review summarizes the multifaceted properties of porphyrins and metalloporphyrins, powerful CD chromophores that are characterized by their intense and red‐shifted Soret band, propensity to undergo π–π stacking, facile incorporation of metals, and ease in varying solubility. Such attributes make porphyrins one of the most attractive and sensitive chromophores used in CD studies. They offer possibilities for studying the stereochemistry of chiral porphyrin assemblies, large organic molecules, biopolymers, and compounds available in miniscule quantities. The tendency of porphyrins to undergo π–π stacking and zinc porphyrins to coordinate with amines enable the CD exciton chirality method to be extended to configurational assignments of flexible compounds containing only one stereogenic center. Various artificial porphyrin receptors have been synthesized for the recognition of biologically important chiral guests such as carbohydrates, amino acids, and their derivatives. The induced CD of the host porphyrin Soret band reflects the identity of guests and binding modes of host/guest complexation with high sensitivity. Chirality 12:237–255, 2000. © 2000 Wiley‐Liss, Inc.

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Section: Uv-vis Spectra Of Porphyrins and Metalloporphyrinsmentioning

confidence: 99%

Section: Uv-vis Spectra Of Porphyrins and Metalloporphyrinsmentioning

confidence: 99%

Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies

2000

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“…In a later work, the synthesis of four porphyrin-peptide conjugates linked to bi-functional cell-penetrating/nuclear-localising sequences was described. 71 Amino-reactive porphyrin 78 was coupled to four hybrid sequences containing a cell penetrating string, Tat (48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58)(59)(60) or Antp (43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58), and a NLS, either the minimal sequence of nucleoplasmin or the SV40-derived GPKKKRKV. TBTU/HOBt/DIEA-mediated coupling on solid support, and TFA-mediated cleavage and deprotection afforded the desired species in 18 to 72% yields.…”

Section: Conjugation Of Amino-reactive Photosensitisers To Poly(lysin...mentioning

confidence: 99%

Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins

Giuntini

Alonso

Boyle

2011

Photochem Photobiol Sci

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The association of photosensitisers to peptides and proteins is a recognised and successful method for enhancing the selectivity and efficacy of photodynamic treatment. The covalent attachment of porphyrins and related macrocycles to peptides and proteins can generate new phototoxic species that allow the concentration of the oxidative damage to the target area, thanks to their enhanced cellular uptake, favourable sub-cellular distribution, and ability to target receptors or enzymes over-expressed by a given tissue or cell. The need to exert control over the regioselectivity of the conjugation led to the exploration of a variety of chemistries; in some cases based on bioorthogonal ligations, in others exploring the reactivity of naturally occurring functional groups. In this review we place a major emphasis on the synthetic strategies adopted to generate such conjugates. All such strategies will be surveyed, together with the methods used to introduce or unmask the appropriate reactive functionalities both on the peptide moiety and the photosensitiser.

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“…The exciton coupled CD appeared for 3 (20 µM in CH 2 Ch, �8 426 = -75.5 and �8 4I6 = 73.2 M-I cm-I ) in the porphyrin region reflecting the chirality of the cyclic peptide. 2 The addition of 6 drastically decreased the split Cotton effects and a weak Cotton effect newly appeared at 424 nm with �8 = 23.7 (Figure 3a).…”

mentioning

confidence: 96%

“…lc, ld We have linked two porphyrins to the natural cyclic peptide, Gramicidin S (Figure 1, 1), and reported the solvent-dependent orientational change of two zinc porphyrins in 3. 2 We wish to report the host-guest capturing by this porphyrin-polypeptide hybrid, which is unique in the following points: 1) the metalloporphyrins are connected via flexible spacers (-(CH 2 ) 3 -) to the peptide and may be brought together by the guest diamine, 2) the peptide framework is rigid with four intramolecular hydrogen bondings, 2 and 3) the self associating character of the peptide might later form the supramolecular multiple host-guest assembly.…”

mentioning

confidence: 99%

Complexation of 4,4′-Dipyridyl Derivatives Changed the Orientations of Metalloporphyrins Linked to the Cyclic Peptide Gramicidin S

Arai¹,

Araki²,

Fukuma³

et al. 2002

Chemistry Letters

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Spatially close porphyrin pair linked by the cyclic peptide Gramicidin S

Cited by 11 publications

References 11 publications

Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies

Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies

Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins

Complexation of 4,4′-Dipyridyl Derivatives Changed the Orientations of Metalloporphyrins Linked to the Cyclic Peptide Gramicidin S

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