110538-19-7

Basic information

• Product Name: homodestruxin B
• Synonyms: homodestruxin B;3-Isopropylcyclo[D-Lac-L-Pro-L-Ile-N-methyl-L-Ile-N-methyl-L-Ala-βAla-]
• CAS NO: 110538-19-7
• Molecular Formula: C₃₁H₅₃N₅O₇
• Molecular Weight: 607.78
• Mol File: 110538-19-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 879.635°C at 760 mmHg
• Flash Point: 485.786°C
• Appearance: /
• Density: 1.162g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: homodestruxin B(CAS DataBase Reference)
• NIST Chemistry Reference: homodestruxin B(110538-19-7)
• EPA Substance Registry System: homodestruxin B(110538-19-7)

Safety Data

• Hazardous Substances Data: 110538-19-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C31H53N5O7/c1-10-19(5)25-30(41)35(9)26(20(6)11-2)31(42)34(8)21(7)27(38)32-15-14-24(37)43-23(17-18(3)4)29(40)36-16-12-13-22(36)28(39)33-25/h18-23,25-26H,10-17H2,1-9H3,(H,32,38)(H,33,39)/t19-,20-,21-,22-,23?,25-,26-/m0/s1

Upstream product

• 41324-66-7 H-Pro-OBzl 
• 383396-97-2 Cbz-Ile-MeIle-MeAla-NHNH-Boc 
• 383396-83-6 Cbz-MeIle-MeAla-NHNH-Boc 
• 383396-87-0 N'-{2-[methyl-(3-methyl-2-methylamino-pentanoyl)-amino]-propionyl}-hydrazinecarboxylic acid tert-butyl ester 
• 55739-22-5 (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid benzyl ester 
• 1026656-54-1 (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid 
• 187753-73-7 (S)-1-((R)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 20312-37-2 (R)-2-hydroxy-4-methylpentanoic acid 
• 383397-11-3 Boc-βAla-Hmp-Pro-Ile-MeIle-MeAlaNHNHBoc 

Relevant articles and documents

Probing host-selective phytotoxicity: Synthesis of destruxin B and several natural analogues

The syntheses of the host-selective phytotoxin destruxin B [cyclo(βAla-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal→MeIle), desmethyldestruxin B (MeVal→Val), hydroxydestruxin B (Hmp→Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal→MeIle, Hmp→Dhmp) are described. In each case, the MeAla-βAla linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-14C]-β-alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.