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Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides

Siva S Panda 1
Siva S Panda
, 
Alexander Anatol'evich Oliferenko 1
Alexander Anatol'evich Oliferenko
, 
Hadi M Marwani 2
Hadi M Marwani
, 
Alan R Katritzky 1, 2
Alan R Katritzky
10.1016/j.mencom.2014.03.002
Published 2014-02-21
Communication , Volume 24, Issue 2, 75-77
4
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Panda S. S. et al. Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides // Mendeleev Communications. 2014. Vol. 24. No. 2. pp. 75-77.
GOST all authors (up to 50) Copy
Panda S. S., Oliferenko A. A., Marwani H. M., Katritzky A. R. Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides // Mendeleev Communications. 2014. Vol. 24. No. 2. pp. 75-77.
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TY - JOUR
DO - 10.1016/j.mencom.2014.03.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.002
TI - Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides
T2 - Mendeleev Communications
AU - Panda, Siva S
AU - Oliferenko, Alexander Anatol'evich
AU - Marwani, Hadi M
AU - Katritzky, Alan R
PY - 2014
DA - 2014/02/21
PB - Mendeleev Communications
SP - 75-77
IS - 2
VL - 24
ER -
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@article{2014_Panda,
author = {Siva S Panda and Alexander Anatol'evich Oliferenko and Hadi M Marwani and Alan R Katritzky},
title = {Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides},
journal = {Mendeleev Communications},
year = {2014},
volume = {24},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.002},
number = {2},
pages = {75--77},
doi = {10.1016/j.mencom.2014.03.002}
}
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Panda, Siva S., et al. “Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides.” Mendeleev Communications, vol. 24, no. 2, Feb. 2014, pp. 75-77. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.002.

Abstract

The ease of intramolecular N-to N-and O-to N-acyl transfers in (N)-acyl isopeptides and (O)-acyl isopeptides was found to be governed by preorganization rationalized in terms of geometrical and energetic characteristics of the linear isopeptide backbone, which depends on the chain length. Intramolecular hydrogen bonding was found another important factor of reactivity able to stabilize the chemical ligation transition state.

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