Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid

G. David Smith; Vladimir Z. Pletnev; William L. Duax; T. M. Balasubramanian; H. E. Bosshard; E. W. Czerwinski; Nancy E. Kendrick; F. Scott Mathews; Garland R. Marshall

doi:10.1021/ja00396a033

Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid

G. David Smith, Vladimir Z. Pletnev, William L. Duax, T. M. Balasubramanian, H. E. Bosshard, E. W. Czerwinski, Nancy E. Kendrick, F. Scott Mathews, Garland R. Marshall

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87 Scopus citations

Abstract

The crystal structures of four peptide fragments (Boc-Pro-Aib-Ala-Aib-OBzl, Boc-Leu-Aib-Pro-OBzl, Boc-Leu-Aib-Pro-OH, and Boc-Gly-Aib-OH) of alamethicin containing five aminoisobutyric acid (Aib) residues have been determined. In all cases, the conformation of the Aib residue is in excellent agreement with the predictions of previous theoretical calculations. Viewed together with other observations in the literature, these data clearly demonstrate that the crystallographically determined average value of ±(50, 42) for (ø, Ψ) for Aib is a low-energy form. Systematic calculations of the possible conformers for acetyl-Aib-Ala-Aib-methylamide show four minima with one corresponding closely to that observed in Boc-Pro-Aib-Ala-Aib-OBzl.

Original language	English
Pages (from-to)	1493-1501
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	103
Issue number	6
DOIs	https://doi.org/10.1021/ja00396a033
State	Published - Mar 1981

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Smith, G. D., Pletnev, V. Z., Duax, W. L., Balasubramanian, T. M., Bosshard, H. E., Czerwinski, E. W., Kendrick, N. E., Mathews, F. S., & Marshall, G. R. (1981). Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid. Journal of the American Chemical Society, 103(6), 1493-1501. https://doi.org/10.1021/ja00396a033

Smith, G. David ; Pletnev, Vladimir Z. ; Duax, William L. ; Balasubramanian, T. M. ; Bosshard, H. E. ; Czerwinski, E. W. ; Kendrick, Nancy E. ; Mathews, F. Scott ; Marshall, Garland R. / Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid. In: Journal of the American Chemical Society. 1981 ; Vol. 103, No. 6. pp. 1493-1501.

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title = "Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid",

abstract = "The crystal structures of four peptide fragments (Boc-Pro-Aib-Ala-Aib-OBzl, Boc-Leu-Aib-Pro-OBzl, Boc-Leu-Aib-Pro-OH, and Boc-Gly-Aib-OH) of alamethicin containing five aminoisobutyric acid (Aib) residues have been determined. In all cases, the conformation of the Aib residue is in excellent agreement with the predictions of previous theoretical calculations. Viewed together with other observations in the literature, these data clearly demonstrate that the crystallographically determined average value of ±(50, 42) for ({\o}, Ψ) for Aib is a low-energy form. Systematic calculations of the possible conformers for acetyl-Aib-Ala-Aib-methylamide show four minima with one corresponding closely to that observed in Boc-Pro-Aib-Ala-Aib-OBzl.",

author = "Smith, {G. David} and Pletnev, {Vladimir Z.} and Duax, {William L.} and Balasubramanian, {T. M.} and Bosshard, {H. E.} and Czerwinski, {E. W.} and Kendrick, {Nancy E.} and Mathews, {F. Scott} and Marshall, {Garland R.}",

year = "1981",

month = mar,

doi = "10.1021/ja00396a033",

language = "English",

volume = "103",

pages = "1493--1501",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

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Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid. / Smith, G. David; Pletnev, Vladimir Z.; Duax, William L.; Balasubramanian, T. M.; Bosshard, H. E.; Czerwinski, E. W.; Kendrick, Nancy E.; Mathews, F. Scott; Marshall, Garland R.

In: Journal of the American Chemical Society, Vol. 103, No. 6, 03.1981, p. 1493-1501.

Research output: Contribution to journal › Article › peer-review

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T1 - Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid

AU - Smith, G. David

AU - Pletnev, Vladimir Z.

AU - Duax, William L.

AU - Balasubramanian, T. M.

AU - Bosshard, H. E.

AU - Czerwinski, E. W.

AU - Kendrick, Nancy E.

AU - Mathews, F. Scott

AU - Marshall, Garland R.

PY - 1981/3

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N2 - The crystal structures of four peptide fragments (Boc-Pro-Aib-Ala-Aib-OBzl, Boc-Leu-Aib-Pro-OBzl, Boc-Leu-Aib-Pro-OH, and Boc-Gly-Aib-OH) of alamethicin containing five aminoisobutyric acid (Aib) residues have been determined. In all cases, the conformation of the Aib residue is in excellent agreement with the predictions of previous theoretical calculations. Viewed together with other observations in the literature, these data clearly demonstrate that the crystallographically determined average value of ±(50, 42) for (ø, Ψ) for Aib is a low-energy form. Systematic calculations of the possible conformers for acetyl-Aib-Ala-Aib-methylamide show four minima with one corresponding closely to that observed in Boc-Pro-Aib-Ala-Aib-OBzl.

AB - The crystal structures of four peptide fragments (Boc-Pro-Aib-Ala-Aib-OBzl, Boc-Leu-Aib-Pro-OBzl, Boc-Leu-Aib-Pro-OH, and Boc-Gly-Aib-OH) of alamethicin containing five aminoisobutyric acid (Aib) residues have been determined. In all cases, the conformation of the Aib residue is in excellent agreement with the predictions of previous theoretical calculations. Viewed together with other observations in the literature, these data clearly demonstrate that the crystallographically determined average value of ±(50, 42) for (ø, Ψ) for Aib is a low-energy form. Systematic calculations of the possible conformers for acetyl-Aib-Ala-Aib-methylamide show four minima with one corresponding closely to that observed in Boc-Pro-Aib-Ala-Aib-OBzl.

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Crystal Structures and Conformational Calculations of Fragments of Alamethicin Containing Aminoisobutyric Acid

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