154561-22-5

Basic information

• Product Name: Z-Aib-OBt
• Synonyms: Z-Aib-OBt
• CAS NO: 154561-22-5
• Molecular Weight: 354.365
• Mol File: 154561-22-5.mol

Chemical Properties

• CAS DataBase Reference: Z-Aib-OBt(CAS DataBase Reference)
• NIST Chemistry Reference: Z-Aib-OBt(154561-22-5)
• EPA Substance Registry System: Z-Aib-OBt(154561-22-5)

Safety Data

• Hazardous Substances Data: 154561-22-5(Hazardous Substances Data)

Upstream product

• 15030-72-5 Z-Aib-OH 
• 2592-95-2 benzotriazol-1-ol 
• 94790-37-1 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 
• 94790-37-1 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 
• 654675-87-3 1-[di(o-tolyl)phosphinyloxy]benzotriazole 
• 54769-58-3 1H-benzo[d][1,2,3]triazol-1-yl 4-nitrobenzenesulfonate 
• 54769-22-1 1-methanesulfonyloxy-1,2,3-benzotriazole 
• 54769-59-4 N-hydroxybenzotriazole ester of benzenesulfonic acid 
• 21978-63-2 1H-benzo[d][1,2,3]triazol-1-yl 4-methanebenzenesulfonate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 79775-03-4 2-<2-(Benzyloxycarboxamido)-2-methylpropionamido>-2-methylpropionsaeure 
• 4576-16-3 2-(1'-((benzyloxycarbonyl)amino)-1'-methylethyl)-4,4-dimethyloxazolone 
• 4512-38-3 Z-(Aib)4-OtBu 
• 4512-42-9 N-[benzyloxycarbonyl]-2-methylalanyl-2-methylalanyl-2-methylalanyl-2-methylalanine 
• 4512-34-9 benzyl N-[8-(4,4-dimethyl-5-oxo-4,5-dihydrooxazol-2-yl)-2,5,5,8-tetramethyl-3,6-dioxo-4,7-diazanon-2-yl]carbamate 
• 83537-94-4 Benzyloxycarbonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert butyl ester 

Relevant articles and documents

Fluorous 2-chloropyridinium salt (Mukaiyama condensation reagent) for amide formation reactions

A new fluorous 2-chloropyridinium hexafluorophosphate was prepared as a modified Mukaiyama condensation reagent, and it was applied in amide formation reactions. Good to excellent purities of amides were obtained after fluorous solid-phase extraction of reaction mixtures without additional chromatography.

Deracemization and the first CD spectrum of a 310-helical peptide made of achiral α-amino-isobutyric acid residues in a chiral membrane mimetic environment

Interaction of the racemic helical homo-octapeptide made by the achiral Cα-methyl alanine (Aib) amino acid with a chiral enantiopure micellar aggregate made of N-dodecylproline led to the deracemization of the helical Aib sequence thus allowing

A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents

A new family of uronium salts (HTMU, HMMU, and HDmPyMU) based on isonitroso Meldrum's acid (HONM) are reported as stand-alone coupling reagents. Amide bond formation with the use of these reagents occurred more quickly than that with other uronium salts as a result of the presence of a neighboring group effect with a cyclic structure. Thus, these novel onium salts were often more effective in the acylation of poor nucleophiles and in the control of optical purity than related Oxyma- and benzotriazole-based reagents. Among the HONM derivatives, HMMU showed the best performance in reducing racemization and assembling demanding sequences such as the Aib-ACP decapeptide or analogues of Leu-enkephalin pentapeptide, Furthermore, the scope and limitations of the use of HONM as an additive in combination with carbodiimides is discussed.

3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene

The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that the new systems were sometimes more and sometimes less effective than previously described systems in the case of stepwise and segment couplings. Applications to assembly of the model decapeptide ACP showed that HDATU was far more effective than HDTU and more effective than HATU under some conditions.

Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents

Organophosphorus esters 9, 10, 14, and 15 prepared via reaction of diethyl- and diphenylphosphoryl chloride, di(o-tolyl)phosphinyl chloride, and 2,8-dimethylphenoxaphosphinyl chloride with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides (20, 21) and a hexapeptide 22. Outstanding utility is also shown for the solid-phase assembly of the ACP decapeptide. Similar results were obtained with the 2- and 4-nitro- and 2,4-dinitrophenylsulfonyl esters derived from HOAt.

The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts

The strict exclusion of tertiary amines during the otherwise sdandard synthetic approach to the synthesis of the quanidinium-type peptide coupling reagents HBTU (X=CH, see scheme) and HATU (X=N) allows the synthesis of the uronium-type isomers of these quanidinium compounds, whose existence was until now pure speculation. These O isomers (O-HBTU and O-HATU) are more efficient coupling reagents than the N isomers. .

New and highly efficient immonium type peptide coupling reagents: Synthesis, mechanism and application

A series of novel immonium type coupling reagents BOMI, BDMP, BPMP, DOMP, SOMP, FOMP and AOMP were designed and synthesized. It was shown that most of these reagents were more efficient in peptide synthesis than conventional methods due to the advantages

Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-isomers

(equation presented) Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.