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Boc-Asp-OH

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  • CAS:13726-67-5
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Boc-Asp-OH Basic information
Product Name:Boc-Asp-OH
Synonyms:BOC-L-ASPARTIC extrapure;N-(tert-Butoxycarbonyl)-L-aspartic acid, Boc-L-aspartic acid;N-BOC-L-Aspartic acid,99%;N.alpha.-tert-Butyloxycarbonylaspartic acid;(2S)-2-[(2-Methylpropan-2-yl)oxycarbonylamino]butanedioic acid;L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-;N-(tert-Butoxycarbonyl)aspartic acid;(2S)-2-(tert-Butoxycarbonylamino)succinic acid
CAS:13726-67-5
MF:C9H15NO6
MW:233.22
EINECS:237-294-7
Product Categories:Aspartic acid [Asp, D];Boc-Amino Acids and Derivative;Amino Acids;Amino Acids (N-Protected);Amino Acid Derivatives;Biochemistry;Boc-Amino Acids;Boc-Amino acid series
Mol File:13726-67-5.mol
Boc-Asp-OH Structure
Boc-Asp-OH Chemical Properties
Melting point 116-118 °C(lit.)
alpha -6 º (c=1, MeOH)
Boiling point 375.46°C (rough estimate)
density 1.3397 (rough estimate)
refractive index 1.4640 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
pka3.77±0.23(Predicted)
form Crystalline Powder
color White to off-white
Optical Rotation[α]20/D 6.0°, c = 1 in methanol
BRN 1913973
Major Applicationpeptide synthesis
InChI1S/C9H15NO6/c1-9(2,3)16-8(15)10-5(7(13)14)4-6(11)12/h5H,4H2,1-3H3,(H,10,15)(H,11,12)(H,13,14)/t5-/m0/s1
InChIKeyKAJBMCZQVSQJDE-YFKPBYRVSA-N
SMILESCC(C)(C)OC(=O)N[C@@H](CC(O)=O)C(O)=O
CAS DataBase Reference13726-67-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36-24/25
WGK Germany 3
HS Code 2924 19 00
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
Boc-Asp-OH English
SigmaAldrich English
ALFA English
Boc-Asp-OH Usage And Synthesis
Chemical Propertieswhite to off-white crystalline powder
UsesN-Boc-L-aspartic acid is an N-Boc-protected form of L-Aspartic acid (A790024). L-Aspartic acid is a nonessential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.
DefinitionChEBI: Nalpha-(tert-butoxycarbonyl)-l-aspartic acid is an aspartic acid derivative.
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
Synthesis
L-Aspartic acid

56-84-8

Di-tert-butyl dicarbonate

24424-99-5

Boc-Asp-OH

13726-67-5

GENERAL STEPS: In a 500 mL single-necked round-bottomed flask, L-aspartic acid (4 g, 30 mmol), 1,4-dioxane (120 mL) and deionized water (60 mL) were mixed to form a heterogeneous solution. Under continuous stirring, 1 M aqueous sodium hydroxide solution was added dropwise until the solution became homogeneous and clarified, indicating complete dissolution of L-aspartic acid. Subsequently, the reaction mixture was cooled in an ice bath and di-tert-butyl dicarbonate (7.2 g, 33 mmol) dissolved in 1,4-dioxane (20 mL) was added slowly and dropwise. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was partially evaporated using a rotary evaporator until the final volume was about 30 mL. ethyl acetate (20 mL) was then added and the aqueous layer was acidified to pH 2 with aqueous potassium bisulfate under ice-bath cooling conditions. the mixture was transferred to a partitioning funnel, and the product was extracted with ethyl acetate (3 aliquots at a time). The organic layers were combined and dried with anhydrous sodium sulfate. Subsequently, the solvent was evaporated using a rotary evaporator and further dried under vacuum overnight to give BOC-L-aspartic acid as a white solid (6 g, 85% yield).1H NMR (600 MHz, DMSO-d6) data: δ 1.38 (s, 9H), 2.51-2.55 (m, 1H), 2.65-2.69 (m, 1H). 4.24-4.28 (m, 1H), 7.05-7.07 (d, 1H, J = 12 Hz), 12.5 (s, 2H).

References[1] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16084 - 16097
[2] Patent: US2017/168042, 2017, A1. Location in patent: Paragraph 0203-0204
[3] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722
[4] Patent: EP1647283, 2006, A1. Location in patent: Page/Page column 5
[5] Chemistry Letters, 1988, # 10, p. 1643 - 1646
Tag:Boc-Asp-OH(13726-67-5) Related Product Information
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