17331-94-1

Basic information

• Product Name: methyl N-[(benzyloxy)carbonyl]serylleucinate
• CAS NO: 17331-94-1
• Molecular Formula: C₁₈H₂₆N₂O₆
• Molecular Weight: 366.4088
• Mol File: 17331-94-1.mol

Chemical Properties

• Boiling Point: 572.5°C at 760 mmHg
• Flash Point: 300°C
• Density: 1.19g/cm³
• Vapor Pressure: 6.05E-14mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: methyl N-[(benzyloxy)carbonyl]serylleucinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-[(benzyloxy)carbonyl]serylleucinate(17331-94-1)
• EPA Substance Registry System: methyl N-[(benzyloxy)carbonyl]serylleucinate(17331-94-1)

Safety Data

• Hazardous Substances Data: 17331-94-1(Hazardous Substances Data)

Upstream product

• 2666-93-5 (S)-Leu-OMe 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 7517-19-3 methyl (L)-leucinate hydrochloride 

Downstream Products

• 75832-11-0 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-O-diphenylphosphoryl-L-seryl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester 
• 75816-53-4 (S)-2-[(S)-2-((2S,3S)-2-{(S)-2-Benzyloxycarbonylamino-3-[(R)-2-methoxycarbonyl-2-(trityl-amino)-ethylsulfanyl]-propionylamino}-3-methyl-pentanoylamino)-3-hydroxy-propionylamino]-4-methyl-pentanoic acid methyl ester 
• 75816-61-4 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine L-hemilanthionine α'-methyl ester hydrochloride 
• 75816-60-3 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine methyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester 
• 75832-12-1 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucine N^α'-trityl-L-hemilanthionine α'-methyl ester 
• 66543-98-4 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucyl-L-hemilanthionine α'-methyl ester 
• 75816-51-2 Nps-Ile-Ser-Leu-OMe 
• 75816-50-1 Z-Ile-Ser-Leu-OMe 
• 107540-52-3 Z-Ala-Ser-Leu-OMe 
• 107540-54-5 Ac-Ala-Ser-Leu-OMe 
• 107540-51-2 Z-Ala-Ser-Leu-OMe 
• 17331-87-2 Z-L-Ser-L-Leu-NH₂ 
• 131458-42-9 Z-NH-CO-CO-Leu-OMe 

Relevant articles and documents

Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation

We report the catalytic direct peptide bond formations via dehydrative condensation of β-hydroxy-α-amino acids, affording the serine, threonine, or β-hydroxyvaline-derived peptides in high to excellent yields with high functional group tolerance, minimum epimerization, and excellent chemoselectivity. The key to the success of these atom-economical transformations is the use of diboronic acid anhydride catalyst for the hydroxy-directed reactions.

Protein backbone modification by novel C(α)-C side-chain scission

α-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)-catalyzed C(α)-C side-chain scission. Facets associated with this novel α-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides - thus acting as Gly equivalents in simulating the α-amidating action of pituitary enzymes - those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C(α) and C side-chain bond), resulting in the generation of α-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C(α)-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [PeP-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX], wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

1,1'-Carbonylbis(3-methylimidazolium) Triflate: An Efficient Reagent for Aminoacylations

Amino acid carboxyl activation and subsequent coupling with nucleophiles frequently suffer from uncertain risks of racemization, complex reagent preparation, or troublesome side-product removal.All of these difficulties are eliminated with a new, simple reagent, 1,1'-carbonylbis(3-methylimidazolium) triflate (CBMIT), obtainable readily by bis-alkylation of carbonyldiimidazole with methyl triflate.Via a highly reactive acyl imidazolium intermediate, CBMIT couples amino acid components or amino acids and alcohols to give peptides and esters, easily isolated in high yield.The reaction medium remains free of any base, and no loss of optical activity is observed.