Comparison of the Effects of (2S,3S)-2,3-Methanomethionine, (2R,3R)-2,3-Methanomethionine, and (2R,3R)-2,3-Methanophenylalanine on the Conformations of Small Peptides

Burgess, Kevin; Ho, Kwok‐Kan; Pal, Biman

doi:10.1021/ja00118a017

Cited by 76 publications

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“…narrowly defined f,c regions, one in each of the quadrants. Moreover, the previously noted, 7 and entirely rational, tendencies for the variation of c with the 2,3-methanoamino acid stereochemistry is unchanged, i.e., the ( 2 S ,3 S ) -isomer tends to adopt conformations with c angles that are either more positive or less negative than those observed for the ( 2 R ,3 R ) -form. The distribution of conformers in each region of f,c space has no quantitative statistical significance, but is it is an indicator of trends.…”

mentioning

confidence: 70%

“…38,39 Thus, the four molecules of interest, F{(2S,3S)-cyThe nmr spectra for the a-methyl derivatives were recorded on a Varian Unity/ 500 spectrometer (500 clo-M}RFa, F{(2R,3R)-cyclo-M}RFa, F{(S)-aMeM}RFa, and F{(R)-a-MeM}RFa were built MHz); nmr data for the 2,3-methanomethionine derivatives were taken from previous work. 6,7 The pepwith positive charges on the amino termini and on the Arg guanidine side chains. Starting conformers tidomimetics were dissolved in DMSO-D 6 (d, 99.99%, Cambridge Isotope Laboratories) to give were obtained by minimization using 1000 steps of the adopted basis Newton-Raphson method, and a 6 mM solutions.…”

Section: Nmr Studies Of the Fourmentioning

confidence: 99%

“…Conversely, if the strucanalogs. We have previously summarized the intriguing antiopiate properties of the FMRFa setural preferences are different, then use of 3-substituted-2,3-methanoamino acids in conjunction with quence, 7 and decided that it meets the latter requirement. Thus the stage was set for the first systema-methylamino acids gives another dimension with which to exert conformational control.…”

Section: Introductionmentioning

confidence: 99%

“…Summaries of the literature associated with conformational effects of cyclopropane amino acids have been made in previous papers in this series. [6][7][8] There is some deliberate overlap between the work reported in this paper and some previous studies; specifically, conformational studies for F{(2S,3S)-cyclo-M}RFa and F{(2R,3R)-cyclo-M}RFa. [6][7][8] However, those studies involved CHARMm 19 molecular simulations with an rms overlay procedure to group structures into families, and a different approach is taken…”

Section: Introductionmentioning

confidence: 99%

“…Throughout, a rant). 7 Despite these differences, important features of the f,c dot plots were maintained. Notably, in continuous dielectric of 1 Å 45 was used to mimic a DMSO environment.…”

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confidence: 99%

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Comparisons of the conformational biases imposed bytrans-2,3-methanomethionine and α-methylmethionine

Burgess¹,

Wen²,

Lim³

et al. 1997

Biopolymers

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A comparative study of four peptidomimetics of the sequence Phe‐Met‐Arg‐Phe‐amide (FMRFa) was performed to compare the conformational bias caused by trans‐2,3‐methanomethionine and α‐methylmethionine stereoisomers. The specific compounds studied were F[(2S,3S)‐cyclo‐M] RFa, F[(2R,3R)‐cyclo‐M]RFa, F[(S)‐α‐MeM]RFa, and F[(R)‐α‐MeM]RFa. Molecular simulations based on CHARMm 22 indicate that γ‐turn, inverse γ‐turn, and α‐helical conformations about the cyclo‐M residue are accessible to the two F[cyclo‐M]RFa stereoisomers. Similar calculations for F[(S)‐α‐MeM]RFa, and F[(R)‐α‐MeM]RFa indicate that the α‐methylamino acids tend to favor α‐helical conformations. The nmr data is presented for the four peptidomimetics. Most informative were the rotating frame nuclear Overhauser effect cross peaks between the NH protons proximal to the methionine surrogates, and the Cβ hydrogens. Overall, these nmr data indicate F[(2S,3S)‐cyclo‐M]RFa and F[(2R,3R)‐cyclo‐M]RFa preferentially adopt inverse γ‐turn and γ‐turn conformations, respectively, whereas F[(S)‐α‐MeM]RFa and F[(R)‐α‐MeM]RFa tend to form partial left‐ and right‐handed helical structures (although energy differences between the two turn structures, and between the two helical structures are likely to be small). It is suggested that the wider NH‐Cα‐CO angle of cyclopropane amino acids and their more severe steric requirements around the Cβ carbons force the peptidomimetic N‐ and C‐termini into the same region of conformational space. This favors C7 turns in the cyclopropane amino acid series relative to the less constrained α‐methyl derivatives. © 1997 John Wiley & Sons, Inc. Biopoly 42: 439–453, 1997

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confidence: 70%

Section: Nmr Studies Of the Fourmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Comparisons of the conformational biases imposed bytrans-2,3-methanomethionine and α-methylmethionine

Burgess¹,

Wen²,

Lim³

et al. 1997

Biopolymers

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Atmospheric pressure chemical ionization multi-stage mass spectrometry in the characterization of stereoisomeric synthons of cyclopropane amino acids

Cristoni¹,

Cativiela

Jiménez

et al. 2000

J. Mass Spectrom.

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The mass spectrometric behaviour of (1S,2R)‐, (1R,2R)‐, (1R,2S)‐ and (1S,2S)‐2‐[(S)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]‐1‐spiro‐{4′[2′‐phenyl‐5′(4′H)‐oxazolone]} cyclopropane (2) and (1S,2R)‐, (1R,2R)‐, (1R,2S)‐ and (1S,2S)‐methyl‐1‐benzamido‐2‐[(S)‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]cyclopropanecarboxylate (3) was studied under atmospheric pression ionization conditions and by multi‐stage mass spectrometric (MSn) experiments performed with an ion trap. Interestingly, by using methanol as solvent, compounds 2 lead to [M + H + CH3OH]+ ions which, as proved by collisional experiments, exhibit the same structure of the corresponding compound 3. MS/MS of [MH]+ ions allows a clear characterization of the different stereoisomers, which give rise to specific fragmentation pathways, rationalized with respect to the structure of the neutral molecules. Copyright © 2000 John Wiley & Sons, Ltd.

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Efficient access to all four stereoisomers of phenylalanine cyclopropane analogues by chiral HPLC

et al. 1999

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Bonded polysaccharide‐derived chiral stationary phases were found to be useful for the preparation of the four stereoisomers of the cyclopropane analogue of phenylalanine (c3Phe) as well as for the direct determination of the enantiomeric purity of c3Phe derivatives by HPLC. Three chiral stationary phases, consisting of cellulose and amylose derivatives chemically bonded on allylsilica gel, were tested. The mixed 10‐undecenoate/3,5‐dimethylphenylcarbamate of cellulose, 10‐undecenoate/3,5‐dimethylphenylcarbamate of amylose and 10‐undecenoate/p‐methylbenzoate of cellulose were the starting polysaccharide derivatives for CSP‐1, CSP‐2, and CSP‐3, respectively. Using mixtures of n‐hexane/chloroform/2‐propanol as mobile phase on a semi‐preparative column (150 mm × 20 mm ID) containing CSP‐2, we separated about 1.7 g of racemic cis‐methyl 1‐tert‐butoxycarbonylamino‐2‐phenylcyclopropanecarboxylate (cis‐6) and 1.2 g of racemic trans‐methyl‐1‐tert‐butoxycarbonylamino‐2‐phenylcycloprop‐anecarboxylate (trans‐6) by successive injections. Chirality 11:583–590, 1999. © 1999 Wiley‐Liss, Inc.

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Comparison of the Effects of (2S,3S)-2,3-Methanomethionine, (2R,3R)-2,3-Methanomethionine, and (2R,3R)-2,3-Methanophenylalanine on the Conformations of Small Peptides

Cited by 76 publications

References 0 publications

Comparisons of the conformational biases imposed bytrans-2,3-methanomethionine and α-methylmethionine

Comparisons of the conformational biases imposed bytrans-2,3-methanomethionine and α-methylmethionine

Atmospheric pressure chemical ionization multi-stage mass spectrometry in the characterization of stereoisomeric synthons of cyclopropane amino acids

Efficient access to all four stereoisomers of phenylalanine cyclopropane analogues by chiral HPLC

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