Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates

Isaac Donkor, Xiaozhang Zheng, Jie Han, Duane Miller

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

2,3-Methanoamino acids are useful probes for studying the bioactive conformation of peptides and for investigating the effect of local conformational constraints on the activity of peptidomimetics. We synthesized all four stereoisomers of Cbz-protected 2,3-methanoleucine for incorporation into peptidomimetic inhibitors of calpain. While the synthesis of 2,3- methanoamino acids has been previously reported, our procedure offers a versatile route in which the pair of diastereomers of each geometric isomer was synthesized from a common intermediate. (C) 2000 Wiley-Liss, Inc.

Original languageEnglish (US)
Pages (from-to)551-557
Number of pages7
JournalChirality
Volume12
Issue number7
DOIs
StatePublished - Jul 6 2000

Fingerprint

Peptidomimetics
Stereoisomerism
Acids
Isomers
Peptides
Conformations
2,3-methanoleucine
calpain inhibitors

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. / Donkor, Isaac; Zheng, Xiaozhang; Han, Jie; Miller, Duane.

In: Chirality, Vol. 12, No. 7, 06.07.2000, p. 551-557.

Research output: Contribution to journalArticle

@article{80ce5c0d6ed24a79a9d4f237f8c41f15,
title = "Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates",
abstract = "2,3-Methanoamino acids are useful probes for studying the bioactive conformation of peptides and for investigating the effect of local conformational constraints on the activity of peptidomimetics. We synthesized all four stereoisomers of Cbz-protected 2,3-methanoleucine for incorporation into peptidomimetic inhibitors of calpain. While the synthesis of 2,3- methanoamino acids has been previously reported, our procedure offers a versatile route in which the pair of diastereomers of each geometric isomer was synthesized from a common intermediate. (C) 2000 Wiley-Liss, Inc.",
author = "Isaac Donkor and Xiaozhang Zheng and Jie Han and Duane Miller",
year = "2000",
month = "7",
day = "6",
doi = "10.1002/1520-636X(2000)12:7<551::AID-CHIR1>3.0.CO;2-C",
language = "English (US)",
volume = "12",
pages = "551--557",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "7",

}

TY - JOUR

T1 - Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates

AU - Donkor, Isaac

AU - Zheng, Xiaozhang

AU - Han, Jie

AU - Miller, Duane

PY - 2000/7/6

Y1 - 2000/7/6

N2 - 2,3-Methanoamino acids are useful probes for studying the bioactive conformation of peptides and for investigating the effect of local conformational constraints on the activity of peptidomimetics. We synthesized all four stereoisomers of Cbz-protected 2,3-methanoleucine for incorporation into peptidomimetic inhibitors of calpain. While the synthesis of 2,3- methanoamino acids has been previously reported, our procedure offers a versatile route in which the pair of diastereomers of each geometric isomer was synthesized from a common intermediate. (C) 2000 Wiley-Liss, Inc.

AB - 2,3-Methanoamino acids are useful probes for studying the bioactive conformation of peptides and for investigating the effect of local conformational constraints on the activity of peptidomimetics. We synthesized all four stereoisomers of Cbz-protected 2,3-methanoleucine for incorporation into peptidomimetic inhibitors of calpain. While the synthesis of 2,3- methanoamino acids has been previously reported, our procedure offers a versatile route in which the pair of diastereomers of each geometric isomer was synthesized from a common intermediate. (C) 2000 Wiley-Liss, Inc.

UR - http://www.scopus.com/inward/record.url?scp=0034046492&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034046492&partnerID=8YFLogxK

U2 - 10.1002/1520-636X(2000)12:7<551::AID-CHIR1>3.0.CO;2-C

DO - 10.1002/1520-636X(2000)12:7<551::AID-CHIR1>3.0.CO;2-C

M3 - Article

VL - 12

SP - 551

EP - 557

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 7

ER -