76689-14-0

Basic information

• Product Name: destruxin E
• Synonyms: destruxin E;3-Oxiranyl-cyclo(D-Lac-L-Pro-L-Ile-N-methyl-L-Val-N-methyl-L-Ala-βAla-);N-[N-[(2R)-1-Oxo-2-hydroxy-3-oxiranylpropyl]-L-Pro-L-Ile-N-methyl-L-Val-N-methyl-L-Ala-]-β-alanine lactone
• CAS NO: 76689-14-0
• Molecular Formula: C29H47N5O8
• Molecular Weight: 593.71
• Mol File: 76689-14-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 909.6°C at 760 mmHg
• Flash Point: 503.9°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 6.03E-34mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: destruxin E(CAS DataBase Reference)
• NIST Chemistry Reference: destruxin E(76689-14-0)
• EPA Substance Registry System: destruxin E(76689-14-0)

Safety Data

• Hazardous Substances Data: 76689-14-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H47N5O8/c1-8-17(4)23-28(39)33(7)24(16(2)3)29(40)32(6)18(5)25(36)30-12-11-22(35)42-21(14-19-15-41-19)27(38)34-13-9-10-20(34)26(37)31-23/h16-21,23-24H,8-15H2,1-7H3,(H,30,36)(H,31,37)

Upstream product

• 1240507-88-3 C₃₆H₅₅N₅O₁₁S 
• 1494545-61-7 C₄₃H₈₁N₅O₁₀Si₂ 
• 1240507-78-1 C₃₂H₅₅N₅O₁₀ 
• 1240507-87-2 C₃₂H₅₃N₅O₉ 
• 651737-62-1 C₂₉H₄₉N₅O₉ 
• 1494545-48-0 (R)-2-((tert-butyldimethylsilyl)oxy)pent-4-enoic acid 
• 1494545-45-7 (R)-2-(tert-butyldimethylsilyloxy)pent-4-enoic acid methyl ester 
• 1494545-40-2 N-[2-(R)-(tert-butyldimethylsiloxy)pent-4-enoyl]-L-proline benzyl ester 
• 1240507-83-8 (S)-HA-Pro-OBn 
• 1494545-81-1 C₁₂H₂₆N₂O₃Si 
• 1494545-83-3 C₁₈H₃₇N₃O₄Si 
• 1494545-35-5 C₂₄H₄₈N₄O₅Si 
• 1240507-79-2 (S)-HA-Pro-OH 
• 1494545-55-9 C₂₀H₃₂N₂O₅Si 

Relevant articles and documents

Solid-Phase Combinatorial Synthesis and Biological Evaluation of Destruxin e Analogues

The solid-phase combinatorial synthesis of cyclodepsipeptide destruxin E has been demonstrated. The combinatorial synthesis of cyclization precursors 8 was achieved by using a split and pool method on SynPhase Lanterns. The products were successfully macrolactonized in parallel in the solution phase by using 2-methyl-6-nitrobenzoic anhydride and 4-(dimethylamino)pyridine N-oxide to afford macrolactones 9, and the subsequent formation of an epoxide in the side chain gave 18 member destruxin E analogues 6. Biological evaluation of analogues 6 indicated that the N-MeAla residue was crucial to the induction of morphological changes in osteoclast-like multinuclear cells (OCLs). Based on structure-activity relationships, azido-containing analogues 15 were then designed for use as a molecular probe. The synthesis and biological evaluation of analogues 15 revealed that 15 b, in which the Ile residue was replaced with a Lys(N3) residue, induced morphological changes in OCLs at a sufficient concentration, and modification around the Ile residue would be tolerated for attachment of a chemical tag toward the target identification of destruxin E (1). Forced to change: The 18 member analogues of destruxin E (see scheme) were successfully synthesized. Biological evaluation of these analogues indicated that the N-MeAla residue was crucial for inducing morphological changes in osteoclast-like multinuclear cells (OCLs). Molecular probes were then prepared by replacing the Ile residue with a Lys(N3) residue for target identification in OCLs.

Synthesis, structure determination, and biological evaluation of destruxin e

The total synthesis of destruxin E (1) has been achieved for the first time, and the stereochemistry of its chiral center at the epoxide has been determined to be (S). The cyclization precursor 3a was synthesized by solid-phase peptide synthesis. Macrolac