Controversy of peptide cyclization from tripeptide

Chung Yin Lin; Subrata Chakraborty; Chia Wei Wong; Dar Fu Tai

doi:10.3390/molecules26020389

Controversy of peptide cyclization from tripeptide

Chung Yin Lin^*, Subrata Chakraborty, Chia Wei Wong, Dar Fu Tai^*

^*Corresponding author for this work

Research Center for Radiation Medicine

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

1 Scopus citations

Abstract

The present investigation reports an attempt to synthesize naturally occurring α-cyclic tripeptide cyclo(Gly-L-Pro-L-Glu) 1, [cyclo(GPE)], previously isolated from the Ruegeria strain of bacteria with marine sponge Suberites domuncula. Three linear precursors, Boc-GPE(OBn)₂, Boc-PE(OBn)G and Boc-E(OBn)GP, were synthesized using a solution phase peptide coupling protocol. Although cyclo(GPE) 1 was our original target, all precursors were dimerized and cyclized at 0^◦C with high dilution to form corresponding α-cyclic hexapeptide, cyclo(GPE(OBn))₂ 7, which was then converted to cyclic hexapeptide cyclo(GPE)₂ 2. Cyclization at higher temperature induced racemization and gave cyclic tripeptide cyclo(GP_DE(OBn)) 9. Structure characteristics of the newly synthesized cyclopeptides were determined using¹H-NMR,¹³C-NMR and high-resolution mass spectrometry. The chemical shift values of carbonyls of 2 and 7 are larger than 170 ppm, indicating the formation of a cyclic hexapeptide.

Original language	English
Article number	389
Journal	Molecules
Volume	26
Issue number	2
DOIs	https://doi.org/10.3390/molecules26020389
State	Published - 02 01 2021

Bibliographical note

Publisher Copyright:
© 2021 by the authors. Li-censee MDPI, Basel, Switzerland.

Keywords

Cyclic hexapeptide
Peptide cyclization
Solution phase synthesis
Tripeptide

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules26020389

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title = "Controversy of peptide cyclization from tripeptide",

abstract = "The present investigation reports an attempt to synthesize naturally occurring α-cyclic tripeptide cyclo(Gly-L-Pro-L-Glu) 1, [cyclo(GPE)], previously isolated from the Ruegeria strain of bacteria with marine sponge Suberites domuncula. Three linear precursors, Boc-GPE(OBn)2, Boc-PE(OBn)G and Boc-E(OBn)GP, were synthesized using a solution phase peptide coupling protocol. Although cyclo(GPE) 1 was our original target, all precursors were dimerized and cyclized at 0◦C with high dilution to form corresponding α-cyclic hexapeptide, cyclo(GPE(OBn))2 7, which was then converted to cyclic hexapeptide cyclo(GPE)2 2. Cyclization at higher temperature induced racemization and gave cyclic tripeptide cyclo(GPDE(OBn)) 9. Structure characteristics of the newly synthesized cyclopeptides were determined using1H-NMR,13C-NMR and high-resolution mass spectrometry. The chemical shift values of carbonyls of 2 and 7 are larger than 170 ppm, indicating the formation of a cyclic hexapeptide.",

keywords = "Cyclic hexapeptide, Peptide cyclization, Solution phase synthesis, Tripeptide",

author = "Lin, {Chung Yin} and Subrata Chakraborty and Wong, {Chia Wei} and Tai, {Dar Fu}",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Li-censee MDPI, Basel, Switzerland.",

year = "2021",

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doi = "10.3390/molecules26020389",

language = "英语",

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T1 - Controversy of peptide cyclization from tripeptide

AU - Lin, Chung Yin

AU - Chakraborty, Subrata

AU - Wong, Chia Wei

AU - Tai, Dar Fu

PY - 2021/1/2

Y1 - 2021/1/2

N2 - The present investigation reports an attempt to synthesize naturally occurring α-cyclic tripeptide cyclo(Gly-L-Pro-L-Glu) 1, [cyclo(GPE)], previously isolated from the Ruegeria strain of bacteria with marine sponge Suberites domuncula. Three linear precursors, Boc-GPE(OBn)2, Boc-PE(OBn)G and Boc-E(OBn)GP, were synthesized using a solution phase peptide coupling protocol. Although cyclo(GPE) 1 was our original target, all precursors were dimerized and cyclized at 0◦C with high dilution to form corresponding α-cyclic hexapeptide, cyclo(GPE(OBn))2 7, which was then converted to cyclic hexapeptide cyclo(GPE)2 2. Cyclization at higher temperature induced racemization and gave cyclic tripeptide cyclo(GPDE(OBn)) 9. Structure characteristics of the newly synthesized cyclopeptides were determined using1H-NMR,13C-NMR and high-resolution mass spectrometry. The chemical shift values of carbonyls of 2 and 7 are larger than 170 ppm, indicating the formation of a cyclic hexapeptide.

AB - The present investigation reports an attempt to synthesize naturally occurring α-cyclic tripeptide cyclo(Gly-L-Pro-L-Glu) 1, [cyclo(GPE)], previously isolated from the Ruegeria strain of bacteria with marine sponge Suberites domuncula. Three linear precursors, Boc-GPE(OBn)2, Boc-PE(OBn)G and Boc-E(OBn)GP, were synthesized using a solution phase peptide coupling protocol. Although cyclo(GPE) 1 was our original target, all precursors were dimerized and cyclized at 0◦C with high dilution to form corresponding α-cyclic hexapeptide, cyclo(GPE(OBn))2 7, which was then converted to cyclic hexapeptide cyclo(GPE)2 2. Cyclization at higher temperature induced racemization and gave cyclic tripeptide cyclo(GPDE(OBn)) 9. Structure characteristics of the newly synthesized cyclopeptides were determined using1H-NMR,13C-NMR and high-resolution mass spectrometry. The chemical shift values of carbonyls of 2 and 7 are larger than 170 ppm, indicating the formation of a cyclic hexapeptide.

KW - Cyclic hexapeptide

KW - Peptide cyclization

KW - Solution phase synthesis

KW - Tripeptide

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U2 - 10.3390/molecules26020389

DO - 10.3390/molecules26020389

M3 - 文章

C2 - 33451079

AN - SCOPUS:85100118628

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

IS - 2

M1 - 389

ER -

Controversy of peptide cyclization from tripeptide

Abstract

Bibliographical note

Keywords

UN SDGs

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