146549-21-5

Basic information

• Product Name: (S)-N-Fmoc-Allylglycine
• Synonyms: Fmoc-Allyglycine;FMOC-L-2-allylglycine Hydrochloride;2-Allyl-N-FMoc-L-glycine, 95%;FMoc-L-Allyglycine FMoc-L-Allyglycine;(S)-2-FMoc-aMino-4-pentenoic acid, FMoc-L-allylglycine;FMoc-a-allyl-Gly-OH;(S)-2-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)pent-4-enoic acid;FMoc-(S)-2-Allylglycine
• CAS NO: 146549-21-5
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.37
• EINECS: 1592732-453-0
• Product Categories: unnatural amino acids;Amino Acids;Unusual amino acids;a-amino
• Mol File: 146549-21-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 137.1 °C
• Boiling Point: 473.68°C (rough estimate)
• Flash Point: 294.3 °C
• Appearance: white to almost white powder
• Density: 1.2486 (rough estimate)
• Vapor Pressure: 1.64E-13mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.72±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: (S)-N-Fmoc-Allylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Fmoc-Allylglycine(146549-21-5)
• EPA Substance Registry System: (S)-N-Fmoc-Allylglycine(146549-21-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 146549-21-5(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white powder

Uses

2-Allyl-N-Fmoc-L-glycine is potentially useful for solid phase peptide synthesis techniques. 2-Allyl-N-Fmoc-L-glycine compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. Reagent in the synthesis of a Dicarba-Analog of Octreotide.

InChI:InChI=1/C20H19NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h2-6,8-11,17-18H,1,7,12H2,(H,21,24)(H,22,23)/t18-/m1/s1

Upstream product

• 198561-07-8 Fmoc-L-propargyl-Gly-OH 
• 16338-48-0 L-allylglycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 127556-06-3 (2R)-N-<(2S)-2-<amino>pent-4-en-1-oyl>bornane-10,2 sultam 
• 740769-74-8 (2S)-N-(2-aminopent-4-enoyl)-(1S,2R)-bornane-10,2-sultam 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 659726-50-8 tert-butyl (2S)-2-[N-(9-phenylfluoren-9-yl)amino]pent-4-enoate 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 146549-17-9 (2S)-2-allyl-N-<(fluoren-9-yl)methoxycarbonyl>glycine prop-2-enyl ester 

Downstream Products

• 903520-19-4 1-(2,4-dimethoxy-benzyl)-8-(9H-fluoren-9-ylmethoxycarbonylamino)-9-oxo-2,3,4,7,8,9-hexahydro-1H-azonine-2-carboxylic acid methyl ester 
• 914486-08-1 (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-methylhex-4-enoic acid 
• 1186094-69-8 Gly-c[Das-c(Δ4Das-Ser-Asp-Pro-Arg)-Arg-Tyr-Arg]-Arg 
• 1186094-66-5 Fmoc-Gly-Pre-c[Das-Ser-Asp-Pro-Arg-Pre-Arg-Tyr-Arg]-Arg 
• 1186094-65-4 Fmoc-Gly-c[Das-Pre-Ser-Asp-Pro-Arg]-Arg-Tyr-Arg-Pre-Arg 
• 1186094-64-3 Fmoc-Gly-Pre-c[Δ4Das-Ser-Asp-Pro-Arg-Pre-Arg-Tyr-Arg]-Arg 
• 1186094-63-2 Fmoc-Gly-c[Δ4Das-Pre-Ser-Asp-Pro-Arg]-Arg-Tyr-Arg-Pre-Arg 
• 1186094-61-0 Fmoc-Gly-Pre-Agl-Ser-Asp-Pro-Arg-Pre-Arg-Tyr-Arg-Agl-Arg 
• 1186094-60-9 Fmoc-Gly-Agl-Pre-Ser-Asp-Pro-Arg-Agl-Arg-Tyr-Arg-Pre-Arg 
• 1186094-68-7 Fmoc-Gly-Crt-c[Das-Ser-Asp-Pro-Arg-Crt-Arg-Tyr-Arg]-Arg 
• 1186094-67-6 Fmoc-Gly-c[Das-Crt-Ser-Asp-Pro-Arg]-Arg-Tyr-Arg-Crt-Arg 
• 1100749-13-0 C₆₆H₈₂N₁₂O₈ 
• 1100749-12-9 C₆₆H₈₀N₁₂O₈ 
• 1100749-11-8 C₆₆H₈₀N₁₂O₈ 

Relevant articles and documents

Novel design of bicyclic β-turn dipeptides on solid-phase supports and synthesis of [3.3.0]-bicyclo[2,3]-leu-enkephalin analogues

(Chemical Equation Presented) External bicyclic β-turn dipeptide mimetics provide an excellent design approach that can offer a rich chiral ensemble of structures with different backbone conformations. We report herein a novel design of a convergent combinatorial synthetic methodology, which is illustrated by the solid-phase synthesis of a series of [3.3.0]-bicyclo [2,3]-Leu-enkephalin analogues. The reactions were optimized and the epimeric configurations were determined by 2D NMR spectroscopy. Biological assays show that these analogues have more potent δ binding affinity and bioactivity for δ vs μ opioid receptor, which may be related to the different conformations preferred by these analogues in our modeling studies.

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripoten