Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

Original languageEnglish (US)
Pages (from-to)91-106
Number of pages16
JournalArkivoc
Volume2014
Issue number4
DOIs
StatePublished - Feb 10 2014

Fingerprint

Threonine
Serine

Keywords

  • Benzotriazole
  • Ligation
  • Peptide
  • Serine
  • Threonine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states. / Panda, Siva S.

In: Arkivoc, Vol. 2014, No. 4, 10.02.2014, p. 91-106.

Research output: Contribution to journalArticle

@article{da45a49ba56045afbaae5390f8b130aa,
title = "Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states",
abstract = "Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.",
keywords = "Benzotriazole, Ligation, Peptide, Serine, Threonine",
author = "Panda, {Siva S.}",
year = "2014",
month = "2",
day = "10",
doi = "10.3998/ark.5550190.p008.632",
language = "English (US)",
volume = "2014",
pages = "91--106",
journal = "Arkivoc",
issn = "1424-6376",
publisher = "Arkat USA",
number = "4",

}

TY - JOUR

T1 - Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states

AU - Panda, Siva S.

PY - 2014/2/10

Y1 - 2014/2/10

N2 - Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

AB - Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

KW - Benzotriazole

KW - Ligation

KW - Peptide

KW - Serine

KW - Threonine

UR - http://www.scopus.com/inward/record.url?scp=84896942934&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84896942934&partnerID=8YFLogxK

U2 - 10.3998/ark.5550190.p008.632

DO - 10.3998/ark.5550190.p008.632

M3 - Article

VL - 2014

SP - 91

EP - 106

JO - Arkivoc

JF - Arkivoc

SN - 1424-6376

IS - 4

ER -