Synthesis of isosteric methylene-oxy pseudodipeptide analogues as novel amide bond surrogate units

E. Rubini; C. Gilon; Z. Selinger; M. Chorev

doi:10.1016/S0040-4020(01)96090-9

Synthesis of isosteric methylene-oxy pseudodipeptide analogues as novel amide bond surrogate units

E. Rubini^*
, C. Gilon
, Z. Selinger
, M. Chorev

^*Corresponding author for this work

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

26 Scopus citations

Abstract

The syntheses of several fully protected dipeptide isosteres which incorporate a methylene-oxy bond replacing the amide bond are described. The novel methylene-oxy modification offers a polar, flexible, proteolytically resistant peptide bond surrogate which can be easily incorporated into biologically active peptides. The standard geometries of the trans-amide, methylene-oxy and methylene-thio units are compared, showing a very close geometrical resemblance of the ψ[CH₂-0] unit to the amide bond.

Original language	English
Pages (from-to)	6039-6045
Number of pages	7
Journal	Tetrahedron
Volume	42
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4020(01)96090-9
State	Published - 1986

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title = "Synthesis of isosteric methylene-oxy pseudodipeptide analogues as novel amide bond surrogate units",

abstract = "The syntheses of several fully protected dipeptide isosteres which incorporate a methylene-oxy bond replacing the amide bond are described. The novel methylene-oxy modification offers a polar, flexible, proteolytically resistant peptide bond surrogate which can be easily incorporated into biologically active peptides. The standard geometries of the trans-amide, methylene-oxy and methylene-thio units are compared, showing a very close geometrical resemblance of the ψ[CH2-0] unit to the amide bond.",

author = "E. Rubini and C. Gilon and Z. Selinger and M. Chorev",

year = "1986",

doi = "10.1016/S0040-4020(01)96090-9",

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T1 - Synthesis of isosteric methylene-oxy pseudodipeptide analogues as novel amide bond surrogate units

AU - Rubini, E.

AU - Gilon, C.

AU - Selinger, Z.

AU - Chorev, M.

PY - 1986

Y1 - 1986

N2 - The syntheses of several fully protected dipeptide isosteres which incorporate a methylene-oxy bond replacing the amide bond are described. The novel methylene-oxy modification offers a polar, flexible, proteolytically resistant peptide bond surrogate which can be easily incorporated into biologically active peptides. The standard geometries of the trans-amide, methylene-oxy and methylene-thio units are compared, showing a very close geometrical resemblance of the ψ[CH2-0] unit to the amide bond.

AB - The syntheses of several fully protected dipeptide isosteres which incorporate a methylene-oxy bond replacing the amide bond are described. The novel methylene-oxy modification offers a polar, flexible, proteolytically resistant peptide bond surrogate which can be easily incorporated into biologically active peptides. The standard geometries of the trans-amide, methylene-oxy and methylene-thio units are compared, showing a very close geometrical resemblance of the ψ[CH2-0] unit to the amide bond.

UR - https://www.scopus.com/pages/publications/0001380312

U2 - 10.1016/S0040-4020(01)96090-9

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AN - SCOPUS:0001380312

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JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Synthesis of isosteric methylene-oxy pseudodipeptide analogues as novel amide bond surrogate units

Abstract

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