An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy

L M A  Rogers; P G  McGivern; A R  Butler; A J  MacRobert; I M  Eggleston

doi:10.1016/j.tet.2005.05.036

An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy

L M A Rogers, P G McGivern, A R Butler, A J MacRobert, I M Eggleston

School of Medicine

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

Abstract

An efficient and cost-effective procedure has been devised for the preparation of urethane-protected 5-aminolaevulinic acid (5-ALA) dipeptide ester derivatives which avoids problems associated with the instability of 5-ALA under basic conditions. The procedure is also applicable to the direct synthesis of N-(alpha)-acetyl amino acid-ALA dipeptides in high enantiomeric purity as potential novel prodrugs for photodynamic therapy (PDT). (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6951-6958
Number of pages	8
Journal	Tetrahedron
Volume	61
DOIs	https://doi.org/10.1016/j.tet.2005.05.036
Publication status	Published - 18 Jul 2005

Keywords

aminolaevulinic acid
peptide
prodrug
photodynamic therapy
PROTOPORPHYRIN-IX
DRUG-DELIVERY
AMINO-ACID
DERIVATIVES
PHOTOSENSITIZERS
PRECURSORS
ESTERS

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10.1016/j.tet.2005.05.036

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title = "An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy",

abstract = "An efficient and cost-effective procedure has been devised for the preparation of urethane-protected 5-aminolaevulinic acid (5-ALA) dipeptide ester derivatives which avoids problems associated with the instability of 5-ALA under basic conditions. The procedure is also applicable to the direct synthesis of N-(alpha)-acetyl amino acid-ALA dipeptides in high enantiomeric purity as potential novel prodrugs for photodynamic therapy (PDT). (c) 2005 Elsevier Ltd. All rights reserved.",

keywords = "aminolaevulinic acid, peptide, prodrug, photodynamic therapy, PROTOPORPHYRIN-IX, DRUG-DELIVERY, AMINO-ACID, DERIVATIVES, PHOTOSENSITIZERS, PRECURSORS, ESTERS",

author = "Rogers, \{L M A\} and McGivern, \{P G\} and Butler, \{A R\} and MacRobert, \{A J\} and Eggleston, \{I M\}",

year = "2005",

month = jul,

day = "18",

doi = "10.1016/j.tet.2005.05.036",

language = "English",

volume = "61",

pages = "6951--6958",

journal = "Tetrahedron",

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TY - JOUR

T1 - An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy

AU - Rogers, L M A

AU - McGivern, P G

AU - Butler, A R

AU - MacRobert, A J

AU - Eggleston, I M

PY - 2005/7/18

Y1 - 2005/7/18

N2 - An efficient and cost-effective procedure has been devised for the preparation of urethane-protected 5-aminolaevulinic acid (5-ALA) dipeptide ester derivatives which avoids problems associated with the instability of 5-ALA under basic conditions. The procedure is also applicable to the direct synthesis of N-(alpha)-acetyl amino acid-ALA dipeptides in high enantiomeric purity as potential novel prodrugs for photodynamic therapy (PDT). (c) 2005 Elsevier Ltd. All rights reserved.

AB - An efficient and cost-effective procedure has been devised for the preparation of urethane-protected 5-aminolaevulinic acid (5-ALA) dipeptide ester derivatives which avoids problems associated with the instability of 5-ALA under basic conditions. The procedure is also applicable to the direct synthesis of N-(alpha)-acetyl amino acid-ALA dipeptides in high enantiomeric purity as potential novel prodrugs for photodynamic therapy (PDT). (c) 2005 Elsevier Ltd. All rights reserved.

KW - aminolaevulinic acid

KW - peptide

KW - prodrug

KW - photodynamic therapy

KW - PROTOPORPHYRIN-IX

KW - DRUG-DELIVERY

KW - AMINO-ACID

KW - DERIVATIVES

KW - PHOTOSENSITIZERS

KW - PRECURSORS

KW - ESTERS

UR - https://www.scopus.com/pages/publications/20444433242

U2 - 10.1016/j.tet.2005.05.036

DO - 10.1016/j.tet.2005.05.036

M3 - Article

SN - 0040-4020

VL - 61

SP - 6951

EP - 6958

JO - Tetrahedron

JF - Tetrahedron

ER -

An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy

Abstract

Keywords

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