137584-40-8

Basic information

• Product Name: L-Isovaline, 3-Methyl-N-[(phenylMethoxy)carbonyl]-
• Synonyms: L-Isovaline, 3-Methyl-N-[(phenylMethoxy)carbonyl]-
• CAS NO: 137584-40-8
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.30496
• Mol File: 137584-40-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Isovaline, 3-Methyl-N-[(phenylMethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Isovaline, 3-Methyl-N-[(phenylMethoxy)carbonyl]-(137584-40-8)
• EPA Substance Registry System: L-Isovaline, 3-Methyl-N-[(phenylMethoxy)carbonyl]-(137584-40-8)

Safety Data

• Hazardous Substances Data: 137584-40-8(Hazardous Substances Data)

Upstream product

• 676268-49-8 (S)-(+)-N-benzyloxycarbonyl-3,4-dimethyl-3-pent-1-enylamine 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 4378-19-2 (S)-α-Methylvaline 
• 1033081-67-2 C₁₉H₂₇NO₄ 

Downstream Products

• 175224-23-4 Z-L-(αMe)Val-F 
• 138142-01-5 (S)-4-isopropyl-4-methyl-oxazolidine-2,5-dione 
• 137584-46-4 2-benzyloxy-4-isopropyl-4-methyl-5(4H)-oxazolone 
• 409320-12-3 Z-L-(αMe)Val-NHEt 
• 409320-07-6 Cbz-L-(α-Me)Val-NH-t-Bu 
• 409320-13-4 Z-L-(αMe)Val-NHMe 
• 711015-19-9 Cbz-L-(αMe)Val-L-Phe-OMe 
• 503564-51-0 Z-L-(αMe)Val-Aib-OtBu 
• 409320-08-7 Z-[L-(αMe)Val]2-NHtBu 
• 409320-09-8 Z-[L-(αMe)Val]3-NHtBu 
• 409320-10-1 Z-[L-(αMe)Val]4-NHtBu 
• 4378-19-2 (S)-α-Methylvaline 
• 1372814-30-6 C₃₁H₄₈BrN₇O₇ 
• 1372814-23-7 Cbz-α-methylvaline-Aib₄-GlyNH2 

Relevant articles and documents

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.

Enantioselective synthesis and enantiomeric amplification of amino acids under prebiotic conditions

(Chemical Equation Presented) A plausible origin of biomolecular homochirality is advanced, where α-methyl amino acids found on meteorites transfer their chirality in the synthesis of normal amino acids. This asymmetry can be amplified to nearly homochiral levels, thus providing the necessary prerequisite for life to start on this planet and elsewhere in the universe.

Role of secondary structure in the asymmetric acylation reaction catalyzed by peptides based on chiral Cα-tetrasubstituted α-amino acids

In a recent series of papers, Miller and co-workers were able to show that His(π-Me)-based, terminally protected peptides are potent catalysts of the asymmetric acyl transfer reaction, useful for the kinetic resolution of alcohols. In a structure-supporting solvent, one of the most active compounds, an Aib-containing tetrapeptide, is folded in a doubly intramolecularly H-bonded β-hairpin motif incorporating a type-II′ β-turn conformation. In this work, we have expanded the study of the Miller tetrapeptide by examining a set of analogues and shorter sequences (dipeptide amides), characterized by chiral Cα-tetrasubstituted α-amino acids of diverging bulkiness and optical configuration. Peptide synthesis in solution, conformational analysis by FT-IR absorption and 1H NMR techniques, and screening of catalytic activity as well have been performed. Our results confirm the close relationship between the β-hairpin 3D-structure and the catalytic activity of the peptides. A tetrapeptide analogue slightly more selective than the Miller compound has been found. However, the terminally protected, industrially more appealing, dipeptide amides are poorly effective.

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximes.

A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.