Maremycin B CAS No. 165877-95-2

Product Description

Maremycin B is a natural product of marine origin, originally isolated from the actinomycete Streptomyces B9173. Although sometimes confused with anthraquinone in early literature, it is now recognized as an indole diketopiperazine alkaloid with a structure based on a rigid bicyclic core containing a 3-hydroxyindol-2-one moiety derived from (2S,3S)-β-methyltryptophan. Together with its co-metabolite maremycin A, it belongs to a small but growing family of indole DKPs that are attracting synthetic and pharmacological attention. Maremycin B exhibits moderate antifungal activity and mild cytotoxicity in preliminary cell-based assays; more importantly, its densely functionalized, stereochemically rich structure has inspired numerous total synthetic studies relying on modern C-H activation, N-heterocyclic carbene catalysis, and other sophisticated strategies. Ongoing biosynthetic studies indicate that its formation utilizes the same NRPS-PKS mechanism as related diketopiperazines such as FR900452, making Maremycin B both a promising lead for antibiotic/antitumor discovery and an attractive target for metabolic engineering.

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Product Use & Characteristics

1. Chemical Identity

   Indole 2,5-diketopiperazine (DKP) alkaloid

   Core: 3-hydroxy-indolin-2-one fused to a cyclic dipeptide (S-methyl-L-cysteine + (2S,3S)-β-methyl-L-tryptophan)

2. Natural Source

   Marine actinomycete Streptomyces sp. strain B9173

3. Uses / Bio-activities

   Antibacterial – active against Gram-positive bacteria

   Antiviral – broad-spectrum potential

   Antitumor / Cytotoxic – inhibits L-929, K562 and HeLa cell lines

4. Biosynthetic Mechanism

   17-gene cluster; NRPS/PKS hybrid pathway

   NRPS assembles the DKP core

   PKS provides cyclopentene-carboxylic acid unit

   MarQ – substrate recognition

   MarI/G/H – stereoselective β-methyl-tryptophan formation

   MarF – N-methylation (D-Trp → L-Trp switch)

5. Synthetic Biology & Engineering

   Engineered Streptomyces strains (Lin Shuangjun group, Shanghai Jiao Tong Univ.) for higher titer and structural diversification

6. Total Synthesis Methods

   6-step NHC/Lewis-acid cascade (Scheidt, 2012) – 17 % yield, 6 linear steps

   15-step C–H activation sequence (Yin & Shi, 2021) – Pd-catalysed C(sp³)–H arylation/methylation, 25 % yield, 15 linear steps

   13-step chiral-pool route (Jia, 2012) – L-isoleucine → β-Me-Trp → DKP, 8.2 % yield

   Cycloaddition approach (Tamura, 2008) – nitrone + 3-ethylidene-indolin-2-one, scalable

7. Key Synthetic Technologies

   C–H functionalisation (Pd, NHC, norbornene)

   Stereoselective bromination / hydroxylation

   Enantioselective [3+2] annulation

   Late-stage azide displacement & Staudinger reduction for amine introduction

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