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RP-66453

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Category Bioactive by-products
Catalog number BBF-03382
CAS
Molecular Weight 616.7
Molecular Formula C33H36N4O8

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

RP-66453 is a secondary peptide metabolite produced by Streptomyces sp. A 9738. It can selectively bind to neurotensin receptor.

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Synonyms RP 66453; RP66453
IUPAC Name 14-amino-17-butan-2-yl-9,32-dihydroxy-15,18,21-trioxo-2-oxa-16,19,22-triazapentacyclo[23.2.2.13,7.15,20.18,12]dotriaconta-1(27),3,5,7(32),8,10,12(31),25,28-nonaene-23-carboxylic acid
Canonical SMILES CCC(C)C1C(=O)NC2CC3=CC(=C(C(=C3)OC4=CC=C(CC(NC2=O)C(=O)O)C=C4)O)C5=C(C=CC(=C5)CC(C(=O)N1)N)O
InChI InChI=1S/C33H36N4O8/c1-3-16(2)28-32(42)35-24-14-19-11-22(21-10-18(6-9-26(21)38)12-23(34)30(40)37-28)29(39)27(15-19)45-20-7-4-17(5-8-20)13-25(33(43)44)36-31(24)41/h4-11,15-16,23-25,28,38-39H,3,12-14,34H2,1-2H3,(H,35,42)(H,36,41)(H,37,40)(H,43,44)
InChI Key LRYMXYNLAMRRTH-UHFFFAOYSA-N
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1. Studies on the total synthesis of RP 66453: synthesis of fully functionalized 15-membered biaryl-containing macrocycle
S Boisnard, A C Carbonnelle, J Zhu Org Lett. 2001 Jun 28;3(13):2061-4. doi: 10.1021/ol016021v.
[structure: see text] Palladium-catalyzed Suzuki cross-coupling, Corey's enantioselective alkylation of glycine template, and macrolactamization are key steps in an efficient synthesis of the 15-membered macrocycle 2.
2. Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions
Mor Ben-Lulu, Eden Gaster, Anna Libman, Doron Pappo Angew Chem Int Ed Engl. 2020 Mar 16;59(12):4835-4839. doi: 10.1002/anie.201913305. Epub 2020 Jan 30.
Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl-bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores.

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