A novel strategy toward [6,5]-bicyclic β-turn dipeptide

Xuyuan Gu; Xuejun Tang; Scott Cowell; Jinfa Ying; Victor J. Hruby

doi:10.1016/S0040-4039(02)01338-2

A novel strategy toward [6,5]-bicyclic β-turn dipeptide

Xuyuan Gu
, Xuejun Tang
, Scott Cowell
, Jinfa Ying
, Victor J. Hruby

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

33 Scopus citations

Abstract

A novel strategy toward the syntheses of [6,5]-bicyclic β-turn dipeptides has been developed starting from δ,ε-unsaturated amino acids. This is the first example showing that this scaffold can be synthesized from a terminal alkene using a trifluoroacetyl protected amino acid. Both enantiomers of the δ,ε-unsaturated amino acid were synthesized by a modified method using Ni(II)-complexes.

Original language	English (US)
Pages (from-to)	6669-6672
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(02)01338-2
State	Published - Sep 9 2002
Externally published	Yes

Keywords

Bicyclic turned dipeptide
Ni(II)-complexes
β-turn mimetic
δ,ε-unsaturated amino acids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)01338-2

Cite this

@article{82491f147e884f9d836df7f18ab6904e,

title = "A novel strategy toward [6,5]-bicyclic β-turn dipeptide",

abstract = "A novel strategy toward the syntheses of [6,5]-bicyclic β-turn dipeptides has been developed starting from δ,ε-unsaturated amino acids. This is the first example showing that this scaffold can be synthesized from a terminal alkene using a trifluoroacetyl protected amino acid. Both enantiomers of the δ,ε-unsaturated amino acid were synthesized by a modified method using Ni(II)-complexes.",

keywords = "Bicyclic turned dipeptide, Ni(II)-complexes, β-turn mimetic, δ,ε-unsaturated amino acids",

author = "Xuyuan Gu and Xuejun Tang and Scott Cowell and Jinfa Ying and Hruby, \{Victor J.\}",

note = "Funding Information: This work was supported by US Public Health Service (DK17420) and the National Institute of Drug Abuse (DA 13449). The DRX 500 MHz NMR spectrometer was obtained by a grant from the NSF (9729350). We thank Professor Dominic V. McGrath for using his group's polarimeter. The views are those of the authors and are not necessarily those of the USPHS.",

year = "2002",

month = sep,

day = "9",

doi = "10.1016/S0040-4039(02)01338-2",

language = "English (US)",

volume = "43",

pages = "6669--6672",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "37",

}

TY - JOUR

T1 - A novel strategy toward [6,5]-bicyclic β-turn dipeptide

AU - Gu, Xuyuan

AU - Tang, Xuejun

AU - Cowell, Scott

AU - Ying, Jinfa

AU - Hruby, Victor J.

N1 - Funding Information: This work was supported by US Public Health Service (DK17420) and the National Institute of Drug Abuse (DA 13449). The DRX 500 MHz NMR spectrometer was obtained by a grant from the NSF (9729350). We thank Professor Dominic V. McGrath for using his group's polarimeter. The views are those of the authors and are not necessarily those of the USPHS.

PY - 2002/9/9

Y1 - 2002/9/9

N2 - A novel strategy toward the syntheses of [6,5]-bicyclic β-turn dipeptides has been developed starting from δ,ε-unsaturated amino acids. This is the first example showing that this scaffold can be synthesized from a terminal alkene using a trifluoroacetyl protected amino acid. Both enantiomers of the δ,ε-unsaturated amino acid were synthesized by a modified method using Ni(II)-complexes.

AB - A novel strategy toward the syntheses of [6,5]-bicyclic β-turn dipeptides has been developed starting from δ,ε-unsaturated amino acids. This is the first example showing that this scaffold can be synthesized from a terminal alkene using a trifluoroacetyl protected amino acid. Both enantiomers of the δ,ε-unsaturated amino acid were synthesized by a modified method using Ni(II)-complexes.

KW - Bicyclic turned dipeptide

KW - Ni(II)-complexes

KW - β-turn mimetic

KW - δ,ε-unsaturated amino acids

UR - https://www.scopus.com/pages/publications/0037048477

UR - https://www.scopus.com/pages/publications/0037048477#tab=citedBy

U2 - 10.1016/S0040-4039(02)01338-2

DO - 10.1016/S0040-4039(02)01338-2

M3 - Article

AN - SCOPUS:0037048477

SN - 0040-4039

VL - 43

SP - 6669

EP - 6672

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

A novel strategy toward [6,5]-bicyclic β-turn dipeptide

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this