Synthetic circularized analogues of bovine pancreatic trypsin inhibitor

Judit Tulla-Puche; Irina V. Getun; Jordi Alsina; Fernando Albericio; George Barany

doi:10.1002/ejoc.200400507

Synthetic circularized analogues of bovine pancreatic trypsin inhibitor

Judit Tulla-Puche, Irina V. Getun, Jordi Alsina, Fernando Albericio, George Barany

Chemistry (Twin Cities)

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

5 Scopus citations

Abstract

Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c-[R]_Smc and c-Cys5[R]_Abu, have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58-residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side-chain anchoring strategy, was cyclized by native chemical ligation.

Original language	English (US)
Pages (from-to)	4541-4544
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	22
DOIs	https://doi.org/10.1002/ejoc.200400507
State	Published - Nov 12 2004

Keywords

Circular proteins
Cyclization
Native chemical ligation
Orthogonal protecting groups
Solid-phase synthesis
Thiolesters

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title = "Synthetic circularized analogues of bovine pancreatic trypsin inhibitor",

abstract = "Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c-[R]Smc and c-Cys5[R]Abu, have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58-residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side-chain anchoring strategy, was cyclized by native chemical ligation.",

keywords = "Circular proteins, Cyclization, Native chemical ligation, Orthogonal protecting groups, Solid-phase synthesis, Thiolesters",

author = "Judit Tulla-Puche and Getun, {Irina V.} and Jordi Alsina and Fernando Albericio and George Barany",

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T1 - Synthetic circularized analogues of bovine pancreatic trypsin inhibitor

AU - Tulla-Puche, Judit

AU - Getun, Irina V.

AU - Alsina, Jordi

AU - Albericio, Fernando

AU - Barany, George

PY - 2004/11/12

Y1 - 2004/11/12

N2 - Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c-[R]Smc and c-Cys5[R]Abu, have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58-residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side-chain anchoring strategy, was cyclized by native chemical ligation.

AB - Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c-[R]Smc and c-Cys5[R]Abu, have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58-residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side-chain anchoring strategy, was cyclized by native chemical ligation.

KW - Circular proteins

KW - Cyclization

KW - Native chemical ligation

KW - Orthogonal protecting groups

KW - Solid-phase synthesis

KW - Thiolesters

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DO - 10.1002/ejoc.200400507

M3 - Article

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JO - Liebigs Annalen der Chemie

JF - Liebigs Annalen der Chemie

SN - 1434-193X

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Synthetic circularized analogues of bovine pancreatic trypsin inhibitor

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