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

Siva S. Panda

doi:10.1016/j.mencom.2014.03.002

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

Siva S. Panda

Chemistry and Physics

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

4 Scopus citations

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.

Original language	English (US)
Pages (from-to)	75-77
Number of pages	3
Journal	Mendeleev Communications
Volume	24
Issue number	2
DOIs	https://doi.org/10.1016/j.mencom.2014.03.002
State	Published - 2014

ASJC Scopus subject areas

Chemistry(all)

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10.1016/j.mencom.2014.03.002

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@article{3b2dacf4e95f45a4b8e9dc46e8d257e1,

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

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.",

author = "Panda, {Siva S.}",

note = "Funding Information: We thank the University of Florida and the Kenan Foundation for financial support. This paper was also funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under Grant no. (24-3-1432/HiCi). The authors, therefore, acknowledge with thanks DSR technical and financial support. We also thank Dr. C. D. Hall for helpful suggestions.",

year = "2014",

doi = "10.1016/j.mencom.2014.03.002",

language = "English (US)",

volume = "24",

pages = "75--77",

journal = "Mendeleev Communications",

issn = "0959-9436",

publisher = "Elsevier BV",

number = "2",

}

TY - JOUR

T1 - Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides

AU - Panda, Siva S.

N1 - Funding Information: We thank the University of Florida and the Kenan Foundation for financial support. This paper was also funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under Grant no. (24-3-1432/HiCi). The authors, therefore, acknowledge with thanks DSR technical and financial support. We also thank Dr. C. D. Hall for helpful suggestions.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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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U2 - 10.1016/j.mencom.2014.03.002

DO - 10.1016/j.mencom.2014.03.002

M3 - Article

AN - SCOPUS:84896962749

SN - 0959-9436

VL - 24

SP - 75

EP - 77

JO - Mendeleev Communications

JF - Mendeleev Communications

IS - 2

ER -

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

Abstract

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