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Cbz-beta-Amino-L-alanine

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Cbz-beta-Amino-L-alanine Basic information
Product Name:Cbz-beta-Amino-L-alanine
Synonyms:L-ALANINE, 3-AMINO-N-[(PHENYLMETHOXY)CARBONYL]-;Z-Dap-OH >=98.0% (NT);Nα-Z-L-2,3-diaminopropionic acid≥ 98% (Assay);CBZ-BETA-AMINO-L-ALANINE;CBZ-L-B-AMINOALANINE;CBZ-L-DAP-OH;3-AMINO-2-BENZYLOXYCARBONYLAMINO-PROPIONIC ACID;Z-L-2,3-DIAMINOPROPIONIC ACID
CAS:35761-26-3
MF:C11H14N2O4
MW:238.24
EINECS:1533716-785-6
Product Categories:Aromatics;Amino Acids & Derivatives
Mol File:35761-26-3.mol
Cbz-beta-Amino-L-alanine Structure
Cbz-beta-Amino-L-alanine Chemical Properties
Melting point ~240 °C (dec.)
Boiling point 463.8±45.0 °C(Predicted)
alpha -39 º (1%, 1N HCl)
density 1.303±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in dilute acid.
pka2.86±0.16(Predicted)
form Solid
color White
Optical Rotation[α]20/D 39±1°, c = 1% in 1 M HCl
Sensitive Hygroscopic
BRN 4486950
Major Applicationpeptide synthesis
InChIInChI=1S/C11H14N2O4/c12-6-9(10(14)15)13-11(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1
InChIKeyFOXRXVSTFGNURG-VIFPVBQESA-N
SMILESC(O)(=O)[C@H](CN)NC(OCC1=CC=CC=C1)=O
CAS DataBase Reference35761-26-3(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
F 3
HS Code 2922.49.3700
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
Cbz-beta-Amino-L-alanine Usage And Synthesis
Chemical PropertiesWhite Solid
UsesNalpha-Benzyloxycarbonyl-L-2,3-diaminopropionic acid is a important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
L-N-Cbz-3-N-Boc-Amino-alanine

16947-84-5

Cbz-beta-Amino-L-alanine

35761-26-3

The general procedure for the synthesis of N(alpha)-Z-L-2,3-diaminopropionic acid from (S)-2-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propionic acid is as follows: 50 g of (S)-N-benzyloxycarbonyl-N'-tert-butoxycarbonyl-2,3-diaminopropionic acid was dissolved in 500 mL of methylene chloride, followed by 50 mL of trifluoroacetic acid. The reaction mixture was stirred at 50 °C for the reaction and subsequently left at room temperature overnight. Upon completion of the reaction, the reaction mixture was concentrated to dryness by rotary evaporator and the evaporation process was repeated to completely remove the solvent.

References[1] Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 2969 - 2977
[2] Patent: CN108452321, 2018, A. Location in patent: Paragraph 0113; 0114; 0115; 0116
Cbz-beta-Amino-L-alanine Preparation Products And Raw materials
Raw materialsL-N-Cbz-3-N-Boc-Amino-alanine-->Trifluoroacetic acid-->Dichloromethane
Preparation ProductsZ-Dap(Fmoc)-OH
Tag:Cbz-beta-Amino-L-alanine(35761-26-3) Related Product Information
L-N-Cbz-3-N-Boc-Amino-alanine Fmoc-Lys(Boc)-OH Boc-Dap-OH Ac-His-OH H2O (S)-3-Amino-2-Cbz-amino-propionic acid tert-butyl ester Z-Dap(Fmoc)-OH DL-2-Aminopropionic anhydride 2,3-Diaminopropionic acid L-2,3-Diaminopropionic acid L-Alanine Cbz-beta-Amino-L-alanine (S)-Methyl 2-N-Cbz-3-N-Boc-propanoate Cbz-beta-amino-D-alanine (S)-N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid Z-L-Dap(Boc)-OBn N-alpha-Benzyloxycarbonyl-N-beta-allyloxycarbonyl-L-2,3-diaminopropionic acid dicyclohexylamine Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochloride (S)-(-)-2-Oxo-1,5-imidazolidinedicarboxylic acid 1-benzyl ester