Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

Panarat Arunrattiyakorn; Banri Ikeda; Teruhiko Nitoda; Hiroshi Kanzaki

doi:10.1271/bbb.60651

Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

Panarat Arunrattiyakorn
, Banri Ikeda
, Teruhiko Nitoda
, Hiroshi Kanzaki

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

9 Citations (Scopus)

Abstract

We have previously isolated cyclo(L-Pro-L-Tyr) and cyclo(L-Phe-L-Pro) from an actinomycete by a novel enzymatic conversion-guided method. Their tetradehydro derivatives, cyclo(ΔPro-ΔTyr) and cyclo(ΔPhe-ΔPro), were enzymatically prepared. Neither of them inhibited cell division, in contrast to other tetradehydro cyclic dipeptides prepared previously. This result suggests that an NH proton in a diketopiperazine ring and/or conformation of the compound are important for the activity.

Original language	English
Pages (from-to)	830-833
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	71
Issue number	3
DOIs	https://doi.org/10.1271/bbb.60651
Publication status	Published - Mar 23 2007
Externally published	Yes

Keywords

dehydro cyclic dipeptide
enzymatic conversion
inhibitor of cell division
diketopiperazine
albonoursin

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10.1271/bbb.60651

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title = "Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division",

abstract = "We have previously isolated cyclo(L-Pro-L-Tyr) and cyclo(L-Phe-L-Pro) from an actinomycete by a novel enzymatic conversion-guided method. Their tetradehydro derivatives, cyclo(ΔPro-ΔTyr) and cyclo(ΔPhe-ΔPro), were enzymatically prepared. Neither of them inhibited cell division, in contrast to other tetradehydro cyclic dipeptides prepared previously. This result suggests that an NH proton in a diketopiperazine ring and/or conformation of the compound are important for the activity.",

keywords = "dehydro cyclic dipeptide, enzymatic conversion, inhibitor of cell division, diketopiperazine, albonoursin",

author = "Panarat Arunrattiyakorn and Banri Ikeda and Teruhiko Nitoda and Hiroshi Kanzaki",

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T1 - Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

AU - Arunrattiyakorn, Panarat

AU - Ikeda, Banri

AU - Nitoda, Teruhiko

AU - Kanzaki, Hiroshi

PY - 2007/3/23

Y1 - 2007/3/23

N2 - We have previously isolated cyclo(L-Pro-L-Tyr) and cyclo(L-Phe-L-Pro) from an actinomycete by a novel enzymatic conversion-guided method. Their tetradehydro derivatives, cyclo(ΔPro-ΔTyr) and cyclo(ΔPhe-ΔPro), were enzymatically prepared. Neither of them inhibited cell division, in contrast to other tetradehydro cyclic dipeptides prepared previously. This result suggests that an NH proton in a diketopiperazine ring and/or conformation of the compound are important for the activity.

AB - We have previously isolated cyclo(L-Pro-L-Tyr) and cyclo(L-Phe-L-Pro) from an actinomycete by a novel enzymatic conversion-guided method. Their tetradehydro derivatives, cyclo(ΔPro-ΔTyr) and cyclo(ΔPhe-ΔPro), were enzymatically prepared. Neither of them inhibited cell division, in contrast to other tetradehydro cyclic dipeptides prepared previously. This result suggests that an NH proton in a diketopiperazine ring and/or conformation of the compound are important for the activity.

KW - dehydro cyclic dipeptide

KW - enzymatic conversion

KW - inhibitor of cell division

KW - diketopiperazine

KW - albonoursin

U2 - 10.1271/bbb.60651

DO - 10.1271/bbb.60651

M3 - Article

C2 - 17341821

SN - 0916-8451

VL - 71

SP - 830

EP - 833

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 3

ER -

Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

Abstract

Keywords

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