A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline
1
Department of Peptidomimetic Research SmithKline Beecham Pharmaceuticals, King of Prussia, PA, 19406, USA
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2
Department of Pysical and Structural Chemistry SmithKline Beecham Pharmaceuticals, King of Prussia, PA, 19406, USA
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Publication type: Journal Article
Publication date: 1993-01-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
5,5-Dimethylproline was designed to induce a cis -peptide bond when incorporated into peptides. In a model dipeptide, it exists 90% as the cis isomer. A convenient synthesis of Boc- DL -5,5-dimethylproline methyl ester is described. This conformationally-constrained amino acid may be expected to exist predominantly in the cis peptide bond isomer when into peptides. The peptide bond in the model peptide Boc-Phe-Me 2 Pro-OMe is shown to be 90% in the cis isomer.
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Magaard V. W. et al. A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline // Tetrahedron Letters. 1993. Vol. 34. No. 3. pp. 381-384.
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Magaard V. W., Sanchez R. M., BEAN J. W., Moore M. J. A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline // Tetrahedron Letters. 1993. Vol. 34. No. 3. pp. 381-384.
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RIS
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TY - JOUR
DO - 10.1016/0040-4039(93)85081-7
UR - https://doi.org/10.1016/0040-4039(93)85081-7
TI - A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline
T2 - Tetrahedron Letters
AU - Magaard, Victoria W
AU - Sanchez, Robert M
AU - BEAN, JOHN W.
AU - Moore, Michael J.
PY - 1993
DA - 1993/01/01
PB - Elsevier
SP - 381-384
IS - 3
VL - 34
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{1993_Magaard,
author = {Victoria W Magaard and Robert M Sanchez and JOHN W. BEAN and Michael J. Moore},
title = {A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline},
journal = {Tetrahedron Letters},
year = {1993},
volume = {34},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/0040-4039(93)85081-7},
number = {3},
pages = {381--384},
doi = {10.1016/0040-4039(93)85081-7}
}
Cite this
MLA
Copy
Magaard, Victoria W., et al. “A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline.” Tetrahedron Letters, vol. 34, no. 3, Jan. 1993, pp. 381-384. https://doi.org/10.1016/0040-4039(93)85081-7.