1011309-61-7

Basic information

• Product Name: (S)-2-amino-2-methyl-4-pentenoicacid
• Synonyms: (S)- 2-(5'-pentenyl) alanine;(S)- 2-(4'-pentenyl) alanine;α-Me-Gly(Pentenyl)-OH;6-Heptenoic acid, 2-amino-2-methyl-, (2S)-;Alpha-Methyl-Gly(Pentenyl)-OH;(S)-2-AMINO-2-METHYL-HEPT-6-ENOIC ACID
• CAS NO: 1011309-61-7
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 129
• EINECS: -0
• Mol File: 1011309-61-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: >200 °C (decomp)
• Boiling Point: 245.3°C at 760 mmHg
• Flash Point: 102.1°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 0.00946mmHg at 25°C
• Refractive Index: 1.485
• PKA: 2.56±0.44(Predicted)
• CAS DataBase Reference: (S)-2-amino-2-methyl-4-pentenoicacid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-amino-2-methyl-4-pentenoicacid(1011309-61-7)
• EPA Substance Registry System: (S)-2-amino-2-methyl-4-pentenoicacid(1011309-61-7)

Safety Data

• Hazardous Substances Data: 1011309-61-7(Hazardous Substances Data)

Usage

General Description

"(S)-2-amino-2-methyl-4-pentenoic acid, also known as "SAMP," is an organic compound that primarily consists of carbon, hydrogen, nitrogen, and oxygen atoms. It is categorized under the alpha amino acids and analogues class. Its physical form is typically a liquid and it has been used in various scientific research and chemical synthesis due to its unique chemical structure. The "S" in its nomenclature denotes the chirality — or geometric orientation — of the molecule, which can significantly influence how it interacts with other chemicals or biological systems. As an amino acid derivative, it may also take part in biochemical reactions involving proteins or other biologically relevant molecules. However, its specific applications may vary depending on the context.

InChI:InChI=1/C5H9NO2/c1-3-5(2,6)4(7)8/h3H,1,6H2,2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 1011309-59-3 2-amino-2-methyl-6-heptenoic acid amide 
• 21889-88-3 hept-6-en-2-one 
• 118757-22-5 2-acetyl-hex-5-enoic acid methyl ester 
• 1009605-77-9 (R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 
• 1379761-96-2 (-)-(3S,5R)-3-methyl-3-(pent-4-enyl)-5-phenylmorpholin-2-one 
• 1119-51-3 bromopentene 
• 7766-48-5 1-iodo-4-pentene 

Downstream Products

• 1011309-82-2 C₁₇H₂₃NO₄ 
• 288617-73-2 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhept-6-enoic acid 

Relevant articles and documents

A reappraisal of the Ni-[(Benzylprolyl)amino]benzophenone complex in the synthesis of α,α-disubstituted amino acid derivatives

α,α-Disubstituted alkenyl amino acid derivatives (e.g. Fmoc-S5-OH) are valuable monomers in the construction of stapled peptide derivatives. Synthetic access to these is possible using the Ni-[(Benzylprolyl)amino]benzophenone (BPB) complex as a chiral auxiliary. We discuss a reappraisal of the use of this, and demonstrate that epimerisation of the proline α-centre occurs during formation of the complex, leading to erosion in the enantiomeric excess of the final product. Modified conditions have been developed, providing the target compounds in high enantiomeric excess.

Influence of α-methylation in constructing stapled peptides with olefin metathesis

Ring-closing metathesis is commonly utilized in peptide macro-cyclization. The influence of α-methylation of the amino acids bearing the olefin moieties has never been systematically studied. In this report, controlled reactions unambiguously indicate that α-methylation at the N-terminus of the metathesis sites is crucial for this reaction to occur. Also, we first elucidated that the E-isomers of stapled peptides are significantly more helical than the Z-isomers.

Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: Synthesis of pipecolic acid and iminosugar derivatives

The preparation of optically pure quaternary piperidines, both fluorinated and non-fluorinated, has been achieved from a chiral imino lactone derived from (R)-phenylglycinol. In the case of the fluorinated derivatives, the addition of (trifluoromethyl)trimethylsilane (TMSCF3) followed by iodoamination and migration of the CF3 group allowed access to four derivatives of α-(trifluoromethyl)pipecolic acid. A theoretical study of the CF 3-group rearrangement has been carried out to help establish the reaction mechanism of this uncommon transformation. Moreover, a route to trifluoromethyl-substituted iminosugars was also developed through the diastereoselective dihydroxylation of suitable synthetic intermediates. Conversely, alkylation of the starting substrate and subsequent cross-metathesis and aza-Michael reactions led to α-alkyl derivatives of the target compounds. Copyright