146453-32-9

Usage

Chemical Properties

White crystal

Upstream product

• 58521-45-2 tert-butoxycarbonyl-L-leucinal 
• 146398-09-6 methyl 4-<(tert-butyloxycarbonyl)amino>-5-(O-tosyl)pentanoate 
• 146398-10-9 methyl 4-<(tert-butyloxycarbonyl)amino>-5-iodopentanoate 
• 146398-08-5 methyl 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate 
• 45214-91-3 N-α-(tert-butoxycarbonyl)-D-glutamic acid γ-methyl ester 
• 27025-22-5 D-glutamic acid-5-methyl ester; hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109579-05-7 [(S)-1-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-3-methyl-butyl]-carbamic acid tert-butyl ester 
• 197006-07-8 (S)-5-[(2-t-butoxycarbonylamino-4-methyl)-pentyl]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 75899-20-6 (C₅H₉O₂)(NHCHCOO)(CH₂C₃H₇)(CO₂C₂H₅) 
• 82010-31-9 (S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester 
• 854102-52-6 [(S,E)-3-methyl-1-styrylbutyl]carbamic acid tert-butyl ester 
• 854102-57-1 [(R)-3-methyl-1-phenethylbutyl]carbamic acid tert-butyl ester 

Downstream Products

• 269078-75-3 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-methylheptanoic acid 
• 207925-00-6 (R)-4-[(S)-4-((R)-4-{(R)-4-[(S)-4-((R)-4-tert-Butoxycarbonylamino-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoylamino}-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoic acid benzyl ester 
• 207924-98-9 (R)-4-[(S)-4-((R)-4-tert-Butoxycarbonylamino-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoic acid benzyl ester 
• 207924-97-8 (R)-4-((S)-4-tert-Butoxycarbonylamino-pentanoylamino)-6-methyl-heptanoic acid benzyl ester 

Relevant academic research and scientific papers

Consequences of isostructural main-chain modifications for the design of antimicrobial foldamers: Helical mimics of host-defense peptides based on a heterogeneous amide/urea backbone

"Chemical Equation Presented" Fraternal twins: Oligoureas and Y-peptides are isosteric, quasi-isostructural helical foldamers endowed with distinct blomolecular recognition properties. Combination of the two backbones to generate urea/amide hybrids (see picture) was found to give more potent yet less cytotoxic antimicrobial helical foldamers.

Potent Antimicrobial Activity of Lipidated Short α,γ-Hybrid Peptides

Herein we report the potent antimicrobial activity of α,γ-hybrid lipopeptides composed of 1:1 alternating α- and γ-amino acids. Along with their potent antimicrobial activity against various Gram-positive and Gram-negative bacteria, these hybrid lipopepti

Asymmetric total synthesis of the caspase-1 inhibitor (-)-berkeleyamide A

The asymmetric total synthesis of (-)-berkeleyamide A (1), a naturally occurring caspase-1 inhibitor, has been achieved by employing Evans' syn-aldol reaction of N-acyl-(4R)-benzyl oxazolidin-2-one 3 as the key step.

Synthesis of non-natural amino acids based on the ruthenium-catalysed oxidation of a phenyl group to carboxylic acid

An efficient method for the synthesis of enantiopure β-, β-, and δ-amino acids with proteinogenic side chains, starting from natural α-amino acids, was developed. The method is based on the ruthenium-catalyzed oxidation of a phenyl group to a carboxylic a

γ-Peptides Forming More Stable Secondary Structures than α-Peptides: Synthesis and Helical NMR-Solution Structure of the γ-Hexapeptide Analog of H-(Val-Ala-Leu)2-OH

For a comparison with the corresponding α- and β-hexapeptides H-(Val-Ala-Leu)2-OH (A) and H-(β-HVal-β-HAla-β-HLeu)2-OH (B), we have now prepared the corresponding γ-hexapeptide 1 built from the homochirally similar (S)-4-aminobutanoic acid, (R)-4-amino-5-methylhexanoic acid, and (R)-4-amino-6-methylheptanoic acid. The precursors were prepared either by double Arndt-Eistert homologation of the protected amino acids Boc-Val-OH, Boc-Ala-OH, and Boc-Leu-OH (Schemes 1 and 2), or by the superior route involving olefination/hydrogenation of the corresponding aldehydes (Boc-valinal, Boc-alaninal, and Boc-leucinal; Scheme 3). Conventional peptide-coupling methodology (EDC/HOBt) furnished the γ-hexapeptide 1 (through the intermediate γ-di- and γ-tripeptide derivatives 9-11). Analysis of NMR measurements in (D5)pyridine and CD3OH solution (COSY, TOCSY, HSQC, HMBC, ROESY) reveals that the γ-hexapeptide 1 adopts a right-handed helical structure ((P)-2.61 helix of ca. 5-A pitch, containing 14-membered H-bonded rings) which is to be compared with the left-handed helix of the corresponding β-peptide B ((M)-31 helix of 5-A pitch, 14-membered H-bonded rings) and with the familiar right-handed, so-called α-helix of α-peptides ((P)-3.61 helix of 5.4-A pitch, 13-membered rings). Like the helix sense, the helix dipole reverses when going from α- (N C) to β- (C N) to γ-peptides (N C). The surprising difference between the natural α-, and the analogous β- and γ-peptides is that the helix stability increases upon homologation of the residues.

Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids

A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields the corresponding γ-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%.

Synthesis of enantiomerically pure β- and γ-amino acids from aspartic and glutamic acid derivatives

An efficient synthesis of enantiomerically pure β- and γ-amino acids starting from commercially available aspartic and glutamic acid derivatives is described. The acid function, α to the amino group, is first transformed to a good leaving group and the pr