Total Synthesis of a Peptide Diatom Sex Pheromone Bearing a Sulfated Aspartic Acid

Andrew M. White; Brett D. Schwartz; Michael G. Gardiner; Lara R. Malins

doi:10.1021/acs.orglett.4c02004

Total Synthesis of a Peptide Diatom Sex Pheromone Bearing a Sulfated Aspartic Acid

Andrew M. White^*, Brett D. Schwartz, Michael G. Gardiner, Lara R. Malins^*

^*Corresponding author for this work

Research School of Chemistry

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

Abstract

The peptide sex-inducing pheromone SIP⁺ (1) bearing an unusual sulfated aspartic acid residue induces sexual reproduction in diatom populations. Herein, we report the first total synthesis of SIP⁺ using both a sulfated building block approach and a solid-phase peptide synthesis (SPPS)-compatible late-stage sulfation strategy to assemble the natural product. The modular approaches provide concise routes to useful quantities of the natural product for future structure activity relationship studies examining the role of SIP⁺ in diatom biology.

Original language	English
Pages (from-to)	6803-6808
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	32
DOIs	https://doi.org/10.1021/acs.orglett.4c02004
Publication status	Published - 5 Jul 2024

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10.1021/acs.orglett.4c02004

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title = "Total Synthesis of a Peptide Diatom Sex Pheromone Bearing a Sulfated Aspartic Acid",

abstract = "The peptide sex-inducing pheromone SIP+ (1) bearing an unusual sulfated aspartic acid residue induces sexual reproduction in diatom populations. Herein, we report the first total synthesis of SIP+ using both a sulfated building block approach and a solid-phase peptide synthesis (SPPS)-compatible late-stage sulfation strategy to assemble the natural product. The modular approaches provide concise routes to useful quantities of the natural product for future structure activity relationship studies examining the role of SIP+ in diatom biology.",

keywords = "Pk, Tyrosine sulfation",

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AU - White, Andrew M.

AU - Schwartz, Brett D.

AU - Gardiner, Michael G.

AU - Malins, Lara R.

PY - 2024/7/5

Y1 - 2024/7/5

N2 - The peptide sex-inducing pheromone SIP+ (1) bearing an unusual sulfated aspartic acid residue induces sexual reproduction in diatom populations. Herein, we report the first total synthesis of SIP+ using both a sulfated building block approach and a solid-phase peptide synthesis (SPPS)-compatible late-stage sulfation strategy to assemble the natural product. The modular approaches provide concise routes to useful quantities of the natural product for future structure activity relationship studies examining the role of SIP+ in diatom biology.

AB - The peptide sex-inducing pheromone SIP+ (1) bearing an unusual sulfated aspartic acid residue induces sexual reproduction in diatom populations. Herein, we report the first total synthesis of SIP+ using both a sulfated building block approach and a solid-phase peptide synthesis (SPPS)-compatible late-stage sulfation strategy to assemble the natural product. The modular approaches provide concise routes to useful quantities of the natural product for future structure activity relationship studies examining the role of SIP+ in diatom biology.

KW - Pk

KW - Tyrosine sulfation

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U2 - 10.1021/acs.orglett.4c02004

DO - 10.1021/acs.orglett.4c02004

M3 - Letter

AN - SCOPUS:85197757457

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SP - 6803

EP - 6808

JO - Organic Letters

JF - Organic Letters

IS - 32

ER -

Total Synthesis of a Peptide Diatom Sex Pheromone Bearing a Sulfated Aspartic Acid

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