Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

Yang Ming Zhang; Yu Ding; Wei Tang; Wei Luo; Min Gu; Wei Lu; Jie Tang; Jian Ping Zuo; Fa Jun Nan

doi:10.1016/j.bmc.2008.09.017

Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

Yang Ming Zhang
, Yu Ding
, Wei Tang
, Wei Luo
, Min Gu
, Wei Lu^*
, Jie Tang
, Jian Ping Zuo
, Fa Jun Nan

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

16 Scopus citations

Abstract

DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-DZ2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)-DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase.

Original language	English
Pages (from-to)	9212-9216
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	20
DOIs	https://doi.org/10.1016/j.bmc.2008.09.017
State	Published - 15 Oct 2008

Keywords

DZ2002
Immunosuppressive potency
S-Adenosyl-l-homocysteine hydrolase
Stereoisomers
Synthesis

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10.1016/j.bmc.2008.09.017

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title = "Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers",

abstract = "DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-DZ2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)-DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase.",

keywords = "DZ2002, Immunosuppressive potency, S-Adenosyl-l-homocysteine hydrolase, Stereoisomers, Synthesis",

author = "Zhang, \{Yang Ming\} and Yu Ding and Wei Tang and Wei Luo and Min Gu and Wei Lu and Jie Tang and Zuo, \{Jian Ping\} and Nan, \{Fa Jun\}",

year = "2008",

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day = "15",

doi = "10.1016/j.bmc.2008.09.017",

language = "英语",

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TY - JOUR

T1 - Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

AU - Zhang, Yang Ming

AU - Ding, Yu

AU - Tang, Wei

AU - Luo, Wei

AU - Gu, Min

AU - Lu, Wei

AU - Tang, Jie

AU - Zuo, Jian Ping

AU - Nan, Fa Jun

PY - 2008/10/15

Y1 - 2008/10/15

N2 - DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-DZ2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)-DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase.

AB - DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-DZ2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)-DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase.

KW - DZ2002

KW - Immunosuppressive potency

KW - S-Adenosyl-l-homocysteine hydrolase

KW - Stereoisomers

KW - Synthesis

UR - https://www.scopus.com/pages/publications/53249089996

U2 - 10.1016/j.bmc.2008.09.017

DO - 10.1016/j.bmc.2008.09.017

M3 - 文章

C2 - 18815049

AN - SCOPUS:53249089996

SN - 0968-0896

VL - 16

SP - 9212

EP - 9216

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 20

ER -

Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

Abstract

Keywords

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