DOI: 10.1111/j.1399-3011.1986.tb01052.x. Conformational properties of <i>trans</i> Ac‐Asn‐Pro‐Tyr‐NHMe and <i>trans</i> Ac‐Tyr‐Pro‐Asn‐NHMe in dimethylsulfoxide and in water determined by multinuclear n.m.r. spectroscopy

Conformational properties of trans Ac‐Asn‐Pro‐Tyr‐NHMe and trans Ac‐Tyr‐Pro‐Asn‐NHMe in dimethylsulfoxide and in water determined by multinuclear n.m.r. spectroscopy

10.1111/j.1399-3011.1986.tb01052.x

Crossref journal-article

Wiley

International Journal of Peptide and Protein Research (311)

Abstract

Vicinal coupling constants between various nuclei provide backbone and side‐chain conformational information for a series of asparagine‐ and tyrosine‐containing peptides in DMSO and in H2O. By enriching Tyr of Ac‐Asn‐Pro‐Tyr‐NHMe with 15N, it has been possible to distinguish between the resonances of the two side‐chain β protons of Tyr. Analysis of the coupling constants in terms of the distributions of side‐chain conformations in these peptides indicates that the addition of Asn to the Pro‐Tyr sequence leads to a less random conformational distribution. When compared to the side‐chain rotamer distribution of Ac‐Asn‐NHMe and Ac‐Tyr‐NHMe, particular Asn and Tyr side‐chain conformations of Ac‐Asn‐Pro‐Tyr‐NHMe are stabilized in dimethylsulfoxide solution. The interaction(s) which stabilize a unique Tyr side‐chain conformation of Ac‐Asn‐Pro‐Tyr‐NHMe in dimethylsulfoxide are not present in Ac‐Ala‐Pro‐Tyr‐NHMe and are unaffected by the addition of Val‐Pro to the C‐terminus of Asn‐Pro‐Tyr. In water, a preferential stabilization of one Asn side‐chain conformation of Ac‐Asn‐Pro‐Tyr‐NHMe is also observed, while the Tyr side‐chain rotamer distribution is similar to that of Ac‐Tyr‐NHMe. An interaction between the Asn side chain and the Pro‐Tyr‐NHMe backbone was previously shown to stabilize a β‐bend conformation at Pro‐Tyr in water. Data are also presented for Ac‐Tyr‐Pro‐Asn‐NHMe, for which local interactions do not stabilize particular backbone conformations in dimethylsulfoxide or in water. The conformations of the peptides studied here are relatively insensitive to temperatures between 27° and 62°, both in dimethylsulfoxide and in water. The sequences Asn‐Pro‐Tyr and Tyr‐Pro‐Asn occur in ribonuclease A, and these tripeptides serve as models for the interactions involved in the folding of this protein.

Bibliography

STIMSON, E. R., MEINWALD, Y. C., MONTELIONE, G. T., & SCHERAGA, H. A. (1986). Conformational properties of trans AcâAsnâProâTyrâNHMe and trans AcâTyrâProâAsnâNHMe in dimethylsulfoxide and in water determined by multinuclear n.m.r. spectroscopy. International Journal of Peptide and Protein Research, 27(6), 569â582. Portico.

Authors 4

E.R. STIMSON (first)
Y.C. MEINWALD (additional)
G.T. MONTELIONE (additional)
H.A. SCHERAGA (additional)

References 32 Referenced 13

10.1021/bi00264a021
10.1021/ja00337a052
10.1021/ja00337a051
10.1016/S0021-9258(19)68195-0
10.1107/S0567740882008346
10.1016/0005-2795(73)90350-4
10.1021/ma60064a038
10.1073/pnas.76.12.6050
10.1021/ja00964a022
10.1002/mrc.1270080503
10.1016/0022-2364(75)90035-9
10.1016/0371-1951(64)80055-2
10.1002/bip.360210508
10.1016/0079-6565(76)80001-5
10.1021/bi00735a013
10.1039/p29720000601
10.1016/0022-2364(76)90052-4
10.1016/S0066-4103(08)60425-1
10.1016/0584-8539(77)80087-1
10.1111/j.1399-3011.1979.tb01866.x
10.1111/j.1399-3011.1983.tb02062.x
10.1021/ma00241a004
10.1002/bip.1979.360180702
10.1016/0003-2697(84)90483-4
10.1002/ange.19750871911
10.1016/0022-2364(75)90061-X
diBlasi R.&Kopple K.D.(1975)J. Chem. Soc. Commun 33–34. (10.1039/C39750000033)
Walter J.A.&Wright J.L.C.(1979)Tetrahedron Lett 3909–3912. (10.1016/S0040-4039(01)86462-5)
10.1002/bip.1976.360151012
10.1002/bip.1976.360151013
{'key': 'e_1_2_1_32_2', 'first-page': '417', 'volume': '289', 'author': 'Vitoux B.', 'year': '1979', 'journal-title': 'C.R. Acad. Sci. Paris. Ser. C'} / C.R. Acad. Sci. Paris. Ser. C by Vitoux B. (1979)
10.1007/978-1-4615-6537-6_5

Dates

Type	When
Created	15 years ago (Aug. 9, 2010, 5:04 p.m.)
Deposited	1 year, 10 months ago (Oct. 21, 2023, 3:31 p.m.)
Indexed	1 year, 7 months ago (Jan. 25, 2024, 12:06 p.m.)
Issued	39 years, 3 months ago (June 1, 1986)
Published	39 years, 3 months ago (June 1, 1986)
Published Online	16 years, 7 months ago (Jan. 12, 2009)
Published Print	39 years, 3 months ago (June 1, 1986)

Funders 0

None

BibTeX

@article{STIMSON_1986, title={Conformational properties of trans Ac‐Asn‐Pro‐Tyr‐NHMe and trans Ac‐Tyr‐Pro‐Asn‐NHMe in dimethylsulfoxide and in water determined by multinuclear n.m.r. spectroscopy}, volume={27}, ISSN={0367-8377}, url={http://dx.doi.org/10.1111/j.1399-3011.1986.tb01052.x}, DOI={10.1111/j.1399-3011.1986.tb01052.x}, number={6}, journal={International Journal of Peptide and Protein Research}, publisher={Wiley}, author={STIMSON, E.R. and MEINWALD, Y.C. and MONTELIONE, G.T. and SCHERAGA, H.A.}, year={1986}, month=jun, pages={569–582} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        1,
        25
      ]
    ],
    "date-time": "2024-01-25T17:06:04Z",
    "timestamp": 1706202364245
  },
  "reference-count": 32,
  "publisher": "Wiley",
  "issue": "6",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2009,
            1,
            12
          ]
        ],
        "date-time": "2009-01-12T00:00:00Z",
        "timestamp": 1231718400000
      },
      "content-version": "vor",
      "delay-in-days": 8261,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1986,
        6
      ]
    ]
  },
  "abstract": "<jats:p>Vicinal coupling constants between various nuclei provide backbone and side\u2010chain conformational information for a series of asparagine\u2010 and tyrosine\u2010containing peptides in DMSO and in H<jats:sub>2</jats:sub>O. By enriching Tyr of Ac\u2010Asn\u2010Pro\u2010Tyr\u2010NHMe with <jats:sup>15</jats:sup>N, it has been possible to distinguish between the resonances of the two side\u2010chain \u03b2 protons of Tyr. Analysis of the coupling constants in terms of the distributions of side\u2010chain conformations in these peptides indicates that the addition of Asn to the Pro\u2010Tyr sequence leads to a less random conformational distribution. When compared to the side\u2010chain rotamer distribution of Ac\u2010Asn\u2010NHMe and Ac\u2010Tyr\u2010NHMe, particular Asn and Tyr side\u2010chain conformations of Ac\u2010Asn\u2010Pro\u2010Tyr\u2010NHMe are stabilized in dimethylsulfoxide solution. The interaction(s) which stabilize a unique Tyr side\u2010chain conformation of Ac\u2010Asn\u2010Pro\u2010Tyr\u2010NHMe in dimethylsulfoxide are not present in Ac\u2010Ala\u2010Pro\u2010Tyr\u2010NHMe and are unaffected by the addition of Val\u2010Pro to the <jats:italic>C</jats:italic>\u2010terminus of Asn\u2010Pro\u2010Tyr. In water, a preferential stabilization of one Asn side\u2010chain conformation of Ac\u2010Asn\u2010Pro\u2010Tyr\u2010NHMe is also observed, while the Tyr side\u2010chain rotamer distribution is similar to that of Ac\u2010Tyr\u2010NHMe. An interaction between the Asn side chain and the Pro\u2010Tyr\u2010NHMe backbone was previously shown to stabilize a \u03b2\u2010bend conformation at Pro\u2010Tyr in water. Data are also presented for Ac\u2010Tyr\u2010Pro\u2010Asn\u2010NHMe, for which local interactions do not stabilize particular backbone conformations in dimethylsulfoxide or in water. The conformations of the peptides studied here are relatively insensitive to temperatures between 27\u00b0 and 62\u00b0, both in dimethylsulfoxide and in water. The sequences Asn\u2010Pro\u2010Tyr and Tyr\u2010Pro\u2010Asn occur in ribonuclease A, and these tripeptides serve as models for the interactions involved in the folding of this protein.</jats:p>",
  "DOI": "10.1111/j.1399-3011.1986.tb01052.x",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2010,
        8,
        9
      ]
    ],
    "date-time": "2010-08-09T21:04:38Z",
    "timestamp": 1281387878000
  },
  "page": "569-582",
  "source": "Crossref",
  "is-referenced-by-count": 13,
  "title": "Conformational properties of <i>trans</i> Ac\u2010Asn\u2010Pro\u2010Tyr\u2010NHMe and <i>trans</i> Ac\u2010Tyr\u2010Pro\u2010Asn\u2010NHMe in dimethylsulfoxide and in water determined by multinuclear n.m.r. spectroscopy",
  "prefix": "10.1111",
  "volume": "27",
  "author": [
    {
      "given": "E.R.",
      "family": "STIMSON",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Y.C.",
      "family": "MEINWALD",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "G.T.",
      "family": "MONTELIONE",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "H.A.",
      "family": "SCHERAGA",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2009,
        1,
        12
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00264a021"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00337a052"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00337a051"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(19)68195-0"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0567740882008346"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0005-2795(73)90350-4"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma60064a038"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1073/pnas.76.12.6050"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00964a022"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/mrc.1270080503"
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0022-2364(75)90035-9"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0371-1951(64)80055-2"
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/bip.360210508"
    },
    {
      "key": "e_1_2_1_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0079-6565(76)80001-5"
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/bi00735a013"
    },
    {
      "key": "e_1_2_1_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/p29720000601"
    },
    {
      "key": "e_1_2_1_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0022-2364(76)90052-4"
    },
    {
      "key": "e_1_2_1_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0066-4103(08)60425-1"
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0584-8539(77)80087-1"
    },
    {
      "key": "e_1_2_1_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1111/j.1399-3011.1979.tb01866.x"
    },
    {
      "key": "e_1_2_1_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1111/j.1399-3011.1983.tb02062.x"
    },
    {
      "key": "e_1_2_1_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00241a004"
    },
    {
      "key": "e_1_2_1_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/bip.1979.360180702"
    },
    {
      "key": "e_1_2_1_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0003-2697(84)90483-4"
    },
    {
      "key": "e_1_2_1_26_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19750871911"
    },
    {
      "key": "e_1_2_1_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0022-2364(75)90061-X"
    },
    {
      "key": "e_1_2_1_28_2",
      "doi-asserted-by": "crossref",
      "unstructured": "diBlasi R.&Kopple K.D.(1975)J. Chem. Soc. Commun 33\u201334.",
      "DOI": "10.1039/C39750000033"
    },
    {
      "key": "e_1_2_1_29_2",
      "doi-asserted-by": "crossref",
      "unstructured": "Walter J.A.&Wright J.L.C.(1979)Tetrahedron Lett 3909\u20133912.",
      "DOI": "10.1016/S0040-4039(01)86462-5"
    },
    {
      "key": "e_1_2_1_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/bip.1976.360151012"
    },
    {
      "key": "e_1_2_1_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/bip.1976.360151013"
    },
    {
      "key": "e_1_2_1_32_2",
      "first-page": "417",
      "volume": "289",
      "author": "Vitoux B.",
      "year": "1979",
      "journal-title": "C.R. Acad. Sci. Paris. Ser. C"
    },
    {
      "key": "e_1_2_1_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-1-4615-6537-6_5"
    }
  ],
  "container-title": "International Journal of Peptide and Protein Research",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1399-3011.1986.tb01052.x",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1986.tb01052.x",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        21
      ]
    ],
    "date-time": "2023-10-21T19:31:10Z",
    "timestamp": 1697916670000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1111/j.1399-3011.1986.tb01052.x"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1986,
        6
      ]
    ]
  },
  "references-count": 32,
  "journal-issue": {
    "issue": "6",
    "published-print": {
      "date-parts": [
        [
          1986,
          6
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1111/j.1399-3011.1986.tb01052.x"
  ],
  "URL": "http://dx.doi.org/10.1111/j.1399-3011.1986.tb01052.x",
  "relation": {},
  "ISSN": [
    "0367-8377"
  ],
  "subject": [],
  "container-title-short": "International Journal of Peptide and Protein Research",
  "published": {
    "date-parts": [
      [
        1986,
        6
      ]
    ]
  }
}