Synthesis and Structure of Cyclic Phosphopeptides Containing a Phosphodiester Linkage

Anita H. van Oijen; Stefan Behrens; Dale F. Mierke; Horst Kessler; Jacques H. van Boom; Rob M.J. Liskamp

doi:10.1021/jo00066a026

Synthesis and Structure of Cyclic Phosphopeptides Containing a Phosphodiester Linkage

Anita H. van Oijen, Stefan Behrens, Dale F. Mierke, Horst Kessler, Jacques H. van Boom, Rob M.J. Liskamp

TUM Emeriti of Excellence

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

6 Scopus citations

Abstract

The synthesis of three cyclic phosphopeptides, which contain a phosphodiester linkage, is described. Starting from either Boc-L-Ser(OBn)-OH or Boc-L-Thr(OBn)-OH, three precursors for the macrocyclization by phosphitylation were prepared. After phosphitylation, using 4-chlorobenzyl bis(N,N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophosphinite, subsequent oxidation and hydrogenolysis the cyclic phosphopeptides 18–20 were obtained. The solution conformation of cyclic phosphopeptide 18 was studied by NMR spectroscopy and restrained molecular dynamics calculations.

Original language	English
Pages (from-to)	3722-3730
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	58
Issue number	14
DOIs	https://doi.org/10.1021/jo00066a026
State	Published - 1993

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@article{974b5ab4238b4b33836ad2adba9c1cd7,

title = "Synthesis and Structure of Cyclic Phosphopeptides Containing a Phosphodiester Linkage",

abstract = "The synthesis of three cyclic phosphopeptides, which contain a phosphodiester linkage, is described. Starting from either Boc-L-Ser(OBn)-OH or Boc-L-Thr(OBn)-OH, three precursors for the macrocyclization by phosphitylation were prepared. After phosphitylation, using 4-chlorobenzyl bis(N,N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophosphinite, subsequent oxidation and hydrogenolysis the cyclic phosphopeptides 18–20 were obtained. The solution conformation of cyclic phosphopeptide 18 was studied by NMR spectroscopy and restrained molecular dynamics calculations.",

author = "\{van Oijen\}, \{Anita H.\} and Stefan Behrens and Mierke, \{Dale F.\} and Horst Kessler and \{van Boom\}, \{Jacques H.\} and Liskamp, \{Rob M.J.\}",

year = "1993",

doi = "10.1021/jo00066a026",

language = "English",

volume = "58",

pages = "3722--3730",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

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TY - JOUR

T1 - Synthesis and Structure of Cyclic Phosphopeptides Containing a Phosphodiester Linkage

AU - van Oijen, Anita H.

AU - Behrens, Stefan

AU - Mierke, Dale F.

AU - Kessler, Horst

AU - van Boom, Jacques H.

AU - Liskamp, Rob M.J.

PY - 1993

Y1 - 1993

N2 - The synthesis of three cyclic phosphopeptides, which contain a phosphodiester linkage, is described. Starting from either Boc-L-Ser(OBn)-OH or Boc-L-Thr(OBn)-OH, three precursors for the macrocyclization by phosphitylation were prepared. After phosphitylation, using 4-chlorobenzyl bis(N,N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophosphinite, subsequent oxidation and hydrogenolysis the cyclic phosphopeptides 18–20 were obtained. The solution conformation of cyclic phosphopeptide 18 was studied by NMR spectroscopy and restrained molecular dynamics calculations.

AB - The synthesis of three cyclic phosphopeptides, which contain a phosphodiester linkage, is described. Starting from either Boc-L-Ser(OBn)-OH or Boc-L-Thr(OBn)-OH, three precursors for the macrocyclization by phosphitylation were prepared. After phosphitylation, using 4-chlorobenzyl bis(N,N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophosphinite, subsequent oxidation and hydrogenolysis the cyclic phosphopeptides 18–20 were obtained. The solution conformation of cyclic phosphopeptide 18 was studied by NMR spectroscopy and restrained molecular dynamics calculations.

UR - https://www.scopus.com/pages/publications/0001732999

U2 - 10.1021/jo00066a026

DO - 10.1021/jo00066a026

M3 - Article

AN - SCOPUS:0001732999

SN - 0022-3263

VL - 58

SP - 3722

EP - 3730

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Synthesis and Structure of Cyclic Phosphopeptides Containing a Phosphodiester Linkage

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