16874-01-4

Upstream product

• 1152-62-1 Cbz-Met-OH 
• 115-11-7 isobutene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 507-19-7 t-butyl bromide 
• 4976-72-1 tert-butyl (2S)-2-amino-4-methylsulfanylbutanoate 
• 501-53-1 benzyl chloroformate 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 4434-61-1 N-(benzyloxycarbonyl)methionine 
• 1152-62-1 Cbz-Met-OH 
• 117751-84-5 1,1-dimethylethyl 4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]-(2S)-butanoate 
• 58569-55-4 met-enkephalin 
• 82362-13-8 H-Phe-Met-OBu^t 
• 82362-15-0 H-Gly-Phe-Met-OBu^t 
• 1448616-22-5 benzyl ((S)-1-(((S)-1-(benzo[d]thiazol-2-yl)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)-4-(methylthio)-1-oxobutan-2-yl)carbamate 
• 117751-80-1 2(S)-tert-butyl 2-N-benzyloxycarbonylamino-3,4-epoxybutanoate 
• 117751-86-7 tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate 
• 82362-16-1 Boc-Tyr-Gly-Gly-Phe-Met-OBu^t 
• 117751-75-4 2'(R),3'(S)-N-(2-acetoxy-3-benzyloxycarbonylamino-3-tert-butoxycarbonylpropyl)N-tert-butoxycarbonylglycine tert-butyl ester 
• 82362-14-9 Z-Gly-Phe-Met-OBu^t 
• 117772-22-2 2'(R),3'(S)-N-(3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-hydroxypropyl)N-tert-butoxycarbonylglycine tert-butyl ester 
• 82362-12-7 Z-Phe-Met-OBu^t 

Relevant academic research and scientific papers

Suzuki-Miyaura cross-coupling reaction of monohalopyridines and L-aspartic acid derivative

Suzuki-Miyaura cross-coupling reaction of halogenated pyridines and a borated L-aspartic acid derivative was conducted. The reactivity of chloro-, bromo-, and iodo-pyridines with substituents at the C2, C3, and C4 positions was investigated. Electron dens

Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study

This work describes the design, synthesis, and evaluation of low-molecular weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(-pyrrolidone-3-yl)-2-benzothiazole (8; Ki = 4.1 nM), in which the P3 valine unit was substituted with a variety of distinct moieties. The resulting series of dipeptide-type inhibitors displayed moderate to good inhibitory activities against 3CLpro. In particular, compounds 26m and 26n exhibited good inhibitory activities with Ki values of 0.39 and 0.33 μM, respectively. These low-molecular weight compounds are attractive leads for the further development of potent peptidomimetic inhibitors with pharmaceutical profiles. Docking studies were performed to model the binding interaction of the compound 26m with the SARS-CoV 3CL protease. The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1′ position, (ii) a γ-lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the N-arylglycine unit and a backbone hydrogen bond donor at the S3-position.

Versatile selective α-carboxylic acid esterification of N-protected amino acids and peptides by alcalase

Under continuous removal of water, the industrial protease Alcalase allows selective synthesis of α-carboxylic acid methyl, ethyl, benzyl, allyl, 2-(trimethylsilyl)ethyl, and tert-butyl esters of amino acids and peptides under mild conditions in very high

Deprotection of t-butyl esters of amino acid derivatives by nitric acid in dichloromethane

The extension of the deprotection procedure of t-butylated carboxyl function using HNO3 in CH2Cl2 to a number of appropriately selected N-Z- derivatives of natural amino acid esters was investigated. The method was found to work effectively with alanine, phenylalanine, serine and the dipeptide aspartame, but the reagent brought about a number of unwanted transformations with tyrosine, methionine and tryptophan. Suitable protection of functions present in the latter ones allowed selective ester dealkylation, but tyrosine underwent unavoidable fast preliminary ring nitration. 2000 Elsevier Science Ltd.

Dicarbonates: Convenient 4-dimethylaminopyridine catalyzed esterification reagents

The DMAP (4-dimethylaminopyridine) catalyzed reaction of dialkyl dicarbonates la-e and carboxylic acids 2 afforded the corresponding esters 5 in good yield.

ISOPROPENYL CHLOROCARBONATE (IPCC) IN AMINO ACID AND PEPTIDE CHEMISTRY: ESTERIFICATION OF N-PROTECTED AMINO ACIDS; APPLICATION TO THE SYNTHESIS OF THE DEPSIPEPTIDE VALINOMYCIN

Esterification of N-protected α-amino acids was achieved via isopropenyl chlorocarbonate (IPCC) activation.In situ alcoholysis of the unstable mixed anhydride intermediate was catalised by 4-(dimethylamino)pyridine (DMAP).Competing isopropenyl ester formation was negligible when using methylene chloride as the solvent.A variety of esters from primary and secondary alcohols were obtained with good yields (60 to 90 percent), and even the more hindered tertiobutyl alcohol gave acceptable yields under more drastic conditions.The improvement in depsipeptide synthetic methodology is illustrated by preparation of the antibiotic valinomycin, using IPCC for ester bond formation, and BOP reagent for peptide coupling and the last-step cyclisation.

CONVENIENT ONE-POT ESTERIFICATION OF N-PROTECTED AMINOACIDS VIA ISOPROPENYL CHLOROFORMATE ACTIVATION.

Activation of N-protected aminoacids by isopropenyl chloroformate leads to esters of primary, secondary and tertiary alcohols with 4-dimethylamino-pyridine as catalyst.