113266-23-2

Basic information

• Product Name: L-Valine, N-[N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-phenylalanyl]-, methyl ester
• CAS NO: 113266-23-2
• Molecular Formula: C25H31N3O6
• Molecular Weight: 469.538
• Mol File: 113266-23-2.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: L-Valine, N-[N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-phenylalanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Valine, N-[N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-phenylalanyl]-, methyl ester(113266-23-2)
• EPA Substance Registry System: L-Valine, N-[N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-phenylalanyl]-, methyl ester(113266-23-2)

Safety Data

• Hazardous Substances Data: 113266-23-2(Hazardous Substances Data)

Upstream product

• 1170-76-9 Z-Gly-(L)-Phe 
• 6306-52-1 L-valine methylester hydrochloride 
• 4070-48-8 L-Valine methyl ester 
• 1330059-32-9 N-benzyloxycarbonylglycine-L-phenylalanine 9-fluorenylmethyl thioester 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 1160842-83-0 (L,L)-Cbz-Gly-Phe-Val-OH 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 63-91-2 L-phenylalanine 
• 67-56-1 methanol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Relevant articles and documents

2-Mercaptopyridone 1-oxide-based uronium salts: New peptide coupling reagents

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Peptide bond formation using polymer-bound BOP

A new polymer-supported BOP (P-BOP) has been prepared starting from the commercially available polystyrene-bound 1-hydroxybenzotriazole (P-HOBt) and successfully used as a solid-supported reagent for peptide-coupling reactions. Compared to BOP, less epime

HOBt and HOAt-derived immonium salts: New and highly efficient coupling reagents for peptide synthesis

Novel HOBt- and HOAt-derived immonium type coupling reagents BDMP, BPMP and AOMP were shown to be very efficient for peptide synthesis with high reactivity, low racemization and good yields. X-Ray analysis indicates BOMI exists as the N-substituted form r

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

Efficient amounts of additives for peptide coupling mediated by a water-soluble carbodiimide in aqueous media

The optimal amounts of HOBt, HOSu, and HONb for enhancement of peptide coupling mediated by EDC in aqueous media were found to be less than equimolar against the C-component or the carbodiimide. A combination of EDC and 0.1 equimolar amount of HOBt was sh

S-(2-Pyrimidinyl)- and S-(2-(4,6-dimethylpyrimidinyl))-1,1,3,3- tetramethylthiouronium hexafluorophosphates: Novel reagents for in situ peptide coupling

Two new reagents for in situ peptide coupling based on the 2-mercaptopyrimidine core have been developed. The readily prepared thiouronium salts were found to promote both peptide and segment coupling efficiently with low racemization/epimerization levels

TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations

Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.

Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o -NosylOXY): A recyclable coupling reagent for racemization-free synthesis of peptide, amide, hydroxamate, and ester

Ubiquitousness of amide and ester functionality makes coupling reactions extremely important. Although numerous coupling reagents are available, methods of preparation of the common and efficient reagents are cumbersome. Those reagents generate a substantial amount of chemical waste and lack recyclability. Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY), the first member of a new generation of coupling reagents, produces byproducts that can be easily recovered and reused for the synthesis of the same reagent, making the method more environmentally friendly and cost-effective. The synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. The synthesis of the difficult sequences, for example, the islet amyloid polypeptide (22-27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH 2) and acyl carrier protein (65-74) fragment (H-Val-Gln-Ala-Ala-Ile- Asp-Tyr-Ile-Asn-Gly-OH), following the solid-phase peptide synthesis (SPPS) protocol and Amyloid β (39-42) peptide (Boc-Val-Val-IIe-Ala-OMe), following solution-phase strategy is demonstrated. Remarkable improvement is noticed with respect to reaction time, yield, and retention of stereochemistry. A mechanistic investigation and recyclability are also described.