Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation

Delin Chen; Kathy Hiu Laam Po; Pilar Blasco; Sheng Chen; Xuechen Li

doi:10.1021/acs.orglett.0c01544

Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation

Delin Chen, Kathy Hiu Laam Po, Pilar Blasco, Sheng Chen, Xuechen Li^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

20 Citations (Scopus)

Abstract

A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100−500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will enhance our understanding of CDA3a and provide valuable antibacterial lead candidates for further development.

Original language	English
Pages (from-to)	4749-4753
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	12
Online published	2 Jun 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c01544
Publication status	Published - 19 Jun 2020

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title = "Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation",

abstract = "A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100−500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will enhance our understanding of CDA3a and provide valuable antibacterial lead candidates for further development.",

author = "Delin Chen and Po, {Kathy Hiu Laam} and Pilar Blasco and Sheng Chen and Xuechen Li",

year = "2020",

month = jun,

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journal = "Organic Letters",

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Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation. / Chen, Delin; Po, Kathy Hiu Laam; Blasco, Pilar et al.
In: Organic Letters, Vol. 22, No. 12, 19.06.2020, p. 4749-4753.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation

AU - Chen, Delin

AU - Po, Kathy Hiu Laam

AU - Blasco, Pilar

AU - Chen, Sheng

AU - Li, Xuechen

PY - 2020/6/19

Y1 - 2020/6/19

N2 - A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100−500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will enhance our understanding of CDA3a and provide valuable antibacterial lead candidates for further development.

AB - A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100−500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will enhance our understanding of CDA3a and provide valuable antibacterial lead candidates for further development.

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U2 - 10.1021/acs.orglett.0c01544

DO - 10.1021/acs.orglett.0c01544

M3 - RGC 21 - Publication in refereed journal

C2 - 32484680

SN - 1523-7060

VL - 22

SP - 4749

EP - 4753

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation

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CRF: Development of Novel Inhibitors Targeting the Resistance Mechanisms of Clinical Superbugs

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Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation

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CRF: Development of Novel Inhibitors Targeting the Resistance Mechanisms of Clinical Superbugs

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