50903-49-6

Upstream product

• 13734-41-3 N-Boc-(S/R)-valine 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 13734-41-3 t-Boc-L-valine 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 96157-57-2 bis(pentafluorophenyl)sulfite 

Downstream Products

• 20902-47-0 N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester 
• 109183-78-0 Boc-Val-Tyr(Bzl)-Chg-His(Dnp)-Pro-Lac-OBzl 
• 170872-82-9 (4E,6E)-(2S,3S,8S,9S)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester 
• 504438-61-3 Boc-L-Val-L-pGlu-OBn 
• 504438-67-9 Boc-L-Val-L-Oxd-OBn 
• 540496-36-4 [(S)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-2-oxo-oxazolidin-4-yl]-acetic acid benzyl ester 
• 78058-06-7 Z-pGlu-Val-Pro-NH₂ 
• 182360-26-5 (S)-2-(1,1-Dimethyl-prop-2-ynylamino)-3-methyl-butyric acid pentafluorophenyl ester 
• 182360-28-7 L-N-(3,3-dimethyl-1-propenyl)valine pentafluorophenyl ester 
• 226067-32-9 C₄₉H₇₄Cl₃N₅O₁₄ 
• 226067-24-9 ((S)-1-{(2E,4E)-(1S,6S,7S)-1-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-7-methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dienylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 226067-11-4 ((S)-1-{(E)-(R)-1-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-iodo-allylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 226067-07-8 (4E,6E)-(2S,3S,8S,9S)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid 
• 226067-34-1 {(S)-1-[(2E,4E)-(1S,6S,7S)-1-((S)-2-Hydroxy-1-methyl-ethyl)-7-methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dienylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Antibacterial and antifungal activities of 2,3-pyrrolidinedione derivatives against oral pathogens

Among the novel approaches applied to antimicrobial drug development, natural product-inspired synthesis plays a major role, by providing biologically validated starting points. Tetramic acids, a class of natural products containing a 2,4-pyrrolidinedione

Multigram-scale synthesis of short peptides via a simplified repetitive solution-phase procedure

(Chemical Equation Presented) A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluoroph

Stereoselective synthesis of pseudotripeptides incorporating uncommon bis-α-aminoacid derivatives and X-ray analysis. Part 3

Stereoselective synthesis of pseudotripeptides 4, 5, 6, 8, 9, 13 and 14, incorporating an uncommon bis(α-aminoacid) derivative, has been accomplished starting from the L-valine derived chiral synthon 1. The configuration of the introduced stereogenic cent

Probing host-selective phytotoxicity: Synthesis and biological activity of phomalide, isophomalide, and dihydrophomalide

The cyclic depsipeptide phomalide [cyclo(Val-(E)-Aba-Hpp-Hmp-(R)-Leu); Aba = 2-amino-2-butenoic acid, Hpp = (2S)-2-hydroxy-3-phenylpropanoic acid, Hmp = (2S)-2-hydroxy-4-methylpentanoic acid] is the host-selective phytotoxin produced by the fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm.] which causes blackleg disease (a devastating disease of several economically important brassica crops). Efficient total syntheses of phomalide, its (Z)-isomer isophomalide, and the two dihydro analogues [(R)-dihydrophomalide and (S)-dihydrophomalide] are described. A [2 + 3] fragment coupling of Cbz-Val-(Z)-Aba with Hpp-Hmp-D-Leu-OBn followed by deprotection and cyclization gave isophomalide which was diastereoselectively isomerized to phomalide by conjugate addition of PhSeH followed by elimination of the corresponding selenoxide. The dihydro analogues were prepared similarly using Cbz-Val-(R)-Abu or Cbz-Val-(S)-Abu (Abu = 2-aminobutanoic acid) in place of Cbz-Val-(Z)-Aba. Biological evaluations of phomalide, isophomalide, and the dihydrophomalides revealed that only phomalide (10-5 M) caused necrotic, chlorotic, and reddish lesions on canola (Brassica napus and Brassica rapa; susceptible to blackleg) leaves whereas no damage was observed on brown mustard (Brassica juncea; resistant to blackleg) or white mustard (Sinapis alba; resistant to blackleg) leaves, even at significantly higher concentrations (10-4 M). Thus, both the presence and configuration of the double bond is crucial for selective phytotoxicity. This is the first reported synthesis of an (E)-Aba-containing natural product, and importantly, the (Z) → (E) isomerization approach should be applicable to other (depsi)peptide targets thereby allowing investigation of the effect of the double-bond configuration on various properties.

Total synthesis of (-)-muscoride A

The recently isolated cyanobacterium metabolite muscoride A was synthesized in 15 steps and in 4.3% overall yield. Novel structural features of this peptide antibiotic include the presence of a threonine-derived bioxazole core and an N-(1,1-dimethyl)allyl ('reverse prenyl') valine residue. In the context of our synthesis, efficient new strategies for the preparation of these segments were developed. The synthesis of two epimers of muscoride A allowed the unambiguous assignment of the relative and absolute configuration of the natural product by NMR and optical rotation analyses.

Bis(pentaluorophenyl) sulfite - A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids

A method was proposed for the preparation of bis(perfluorophenyl) sulfite, an effective new reagent for the synthesis of pentafluorophenyl esters of N-protected amino acids without racemization.

Prevention of Diketopiperazine Formation in Peptide Synthesis by a Simultaneous Deprotection-Coupling Procedure: Entrapment of Reactive Nucleophilic Species by in situ Acylation

Hydrogenolysis of Z-amino acid-D-Pro-OMe dipeptides in the presence of acetic acid results, almost quantitatively, in the formation of diketopiperazines, whereas in the presence of Boc- or 2-(trimethylsilyl)ethoxycarbonyl protected amino acid pentafluorop