New and Efficient Coupling Method for the Synthesis of Peptides Bearing the Norstatine Residue and Their Analogs

Iwao Ojima; Chung Ming Sun; Young Hoon Park

doi:10.1021/jo00085a008

New and Efficient Coupling Method for the Synthesis of Peptides Bearing the Norstatine Residue and Their Analogs

Iwao Ojima
, Chung Ming Sun
, Young Hoon Park

Chemistry

Stony Brook University

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

43 Scopus citations

Abstract

Novel ring-opening coupling reactions of enantiomerically pure (3R,4S)-1-(tert-butoxycarbonyl)-3-hydroxy β-lactams 1 with various (S)-amino acid esters 2 including proline methyl ester proceed smoothly at ambient temperature to give the corresponding dipeptides 3 bearing the norstatine residue and its analogs in excellent yields. This new coupling method is applicable to solid-phase peptide syntheses.

Original language	English
Pages (from-to)	1249-1250
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	59
Issue number	6
DOIs	https://doi.org/10.1021/jo00085a008
State	Published - Mar 1 1994

Access to Document

10.1021/jo00085a008

Cite this

@article{07d8598cf8254da2812dad29c3d52d1e,

title = "New and Efficient Coupling Method for the Synthesis of Peptides Bearing the Norstatine Residue and Their Analogs",

abstract = "Novel ring-opening coupling reactions of enantiomerically pure (3R,4S)-1-(tert-butoxycarbonyl)-3-hydroxy β-lactams 1 with various (S)-amino acid esters 2 including proline methyl ester proceed smoothly at ambient temperature to give the corresponding dipeptides 3 bearing the norstatine residue and its analogs in excellent yields. This new coupling method is applicable to solid-phase peptide syntheses.",

author = "Iwao Ojima and Sun, \{Chung Ming\} and Park, \{Young Hoon\}",

year = "1994",

month = mar,

day = "1",

doi = "10.1021/jo00085a008",

language = "English",

volume = "59",

pages = "1249--1250",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "6",

}

TY - JOUR

T1 - New and Efficient Coupling Method for the Synthesis of Peptides Bearing the Norstatine Residue and Their Analogs

AU - Ojima, Iwao

AU - Sun, Chung Ming

AU - Park, Young Hoon

PY - 1994/3/1

Y1 - 1994/3/1

N2 - Novel ring-opening coupling reactions of enantiomerically pure (3R,4S)-1-(tert-butoxycarbonyl)-3-hydroxy β-lactams 1 with various (S)-amino acid esters 2 including proline methyl ester proceed smoothly at ambient temperature to give the corresponding dipeptides 3 bearing the norstatine residue and its analogs in excellent yields. This new coupling method is applicable to solid-phase peptide syntheses.

AB - Novel ring-opening coupling reactions of enantiomerically pure (3R,4S)-1-(tert-butoxycarbonyl)-3-hydroxy β-lactams 1 with various (S)-amino acid esters 2 including proline methyl ester proceed smoothly at ambient temperature to give the corresponding dipeptides 3 bearing the norstatine residue and its analogs in excellent yields. This new coupling method is applicable to solid-phase peptide syntheses.

UR - https://www.scopus.com/pages/publications/0000467936

U2 - 10.1021/jo00085a008

DO - 10.1021/jo00085a008

M3 - Article

AN - SCOPUS:0000467936

SN - 0022-3263

VL - 59

SP - 1249

EP - 1250

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

New and Efficient Coupling Method for the Synthesis of Peptides Bearing the Norstatine Residue and Their Analogs

Abstract

Access to Document

Other files and links

Fingerprint

Cite this