The Cyclic Peptides: Structure, Conformation, and Function

Ovchinnikov, Yu.A.; Иванов, В. Т.

doi:10.1016/b978-0-12-516305-7.50009-5

Cited by 49 publications

(20 citation statements)

References 1,472 publications

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“…Six representative strains of methylotrophic methanogenic species were examined for sensitivity to valinomycin, an antibiotic that acts as a K+ uniporter (34). The growth rates of these six strains were measured in the presence and absence of 0.8 puM valinomycin in medium with 20 mM trimethylamine as the sole energy source and 10 mM total K+ (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Potassium extrusion by the moderately halophilic and alkaliphilic methanogen methanolobus taylorii GS-16 and homeostasis of cytosolic pH

Boone

1994

J Bacteriol

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Methanolobus taylorii GS-16, a moderately halophilic and alkaliphilic methanogen, grows over a wide pH range, from 6.8 to 9.0. Cells suspended in medium with a pH above 8.2 reversed their transmembrane pH gradient (ApH), making their cytosol more acidic than the medium. The decreased energy in the proton motive force due to the reversed ApH was partly compensated by an increased electric membrane potential (A*

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Section: Resultsmentioning

confidence: 99%

Potassium extrusion by the moderately halophilic and alkaliphilic methanogen methanolobus taylorii GS-16 and homeostasis of cytosolic pH

Boone

1994

J Bacteriol

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“…The best known structures in this category belong to the ion-selective antibiotics, valino- 3 , where Hyiv = α-hydroxyisovaleric acid and Lac = lactic acid, and the closely related enniatin family, enniatin A, cyclo(D-Hyiv-MeIle) 3 The early thrust in the synthesis of these molecules came from the Shemyakin group in Russia [143], and the need to improve the performance of valinomycin derivatives in selective ion electrode applications has up-dated the procedures [144]. Macrocyclization of linear depside precursors in this case was carried out at 90°C with a C-terminal Hyiv carboxyl group activated as a pentafluorophenyl ester.…”

Section: Cyclodepsipeptidesmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

417

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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“…Let x and y be two diastereomeric sequences. According to the literature I'l) (1) and I ' : ( 1) are of the same order of magnitude. In the ratio K , / K , we only take into account the main contributions and neglect the angular correlation factor.…”

Section: Ddll-pr04mentioning

confidence: 96%

“…( r ) is the probability per unit volume for the end-to-end vector of the chain x to take the value r. I ' : (1) is the angular correlation factor, cCx the symetry number, and NA Avogadro's number. Let x and y be two diastereomeric sequences.…”

Section: Ddll-pr04mentioning

confidence: 99%

Conformation and formation tendency of the cyclotetrapeptide cyclo(D‐pro‐D‐pro‐L‐pro‐L‐pro): Experimental results and molecular modeling studies

et al. 1991

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The title compound represents the smallest member of cyclic proline peptides corresponding to the general formula c(DDLL-Pro4)n with a strictly D,D,L,L double-alternating sequence of the chiral amino acid residues. The cyclopeptides with n greater than or equal to 2 could be synthesized from both DDLL-Pro4 (1) and DLLD-Pro4 (2). The cyclic monomer (n = 1) resulted only from 2, whereas not even a trace could be found by cyclization of 1. The peptide exists in a strongly strained Ci symmetrical conformation (x-ray analysis) with alternating cis and trans peptide bonds (ctct form I). The cis peptide bonds deviate from planarity (omega = 22 degrees); two of the pyrrolidine rings show a "South" conformation (phi = -94 degrees), whereas the other residues exhibit C alpha-endo puckering (phi = -124 degrees). Two of the psi angles surprisingly occur at +41 degrees (anti-cis'), the others are located in the trans' region. A quantitative ring opening occurs with trifluoroacetic acid at room temperature. In solution the existence of an isomeric ctcc sequence (form Ia) is indicated. Dreiding model studies also suggested a favorable conformation with a tctc sequence (form II). Consequently, we performed molecular mechanics calculations, based on the CHARMM force field and semiempirical quantum mechanical AM1 calculations (MOPAC program). Pronounced differences in the backbone parameters were found using these two methods. However, the theoretical studies evidenced the experimentally obtained differences in the cyclization tendencies of the linear precursors.

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The Cyclic Peptides: Structure, Conformation, and Function

Cited by 49 publications

References 1,472 publications

Potassium extrusion by the moderately halophilic and alkaliphilic methanogen methanolobus taylorii GS-16 and homeostasis of cytosolic pH

Potassium extrusion by the moderately halophilic and alkaliphilic methanogen methanolobus taylorii GS-16 and homeostasis of cytosolic pH

The cyclization of peptides and depsipeptides

Conformation and formation tendency of the cyclotetrapeptide cyclo(D‐pro‐D‐pro‐L‐pro‐L‐pro): Experimental results and molecular modeling studies

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