Boc-Dap-OH Chemical Properties

Melting point:

210 °C (dec.)

alpha 

-5.5 º (c=1, acetic acid)

Boiling point:

364.4±37.0 °C(Predicted)

Density 

1.189±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly, Heated, Sonicated), Water (Sparingly, Heated, Sonicated)

form 

Solid

pka

2.88±0.16(Predicted)

color 

White to Off-White

optical activity

[α]20/D +5.5±1°, c = 1% in methanol: water (1:1)

BRN 

4182136

InChI

InChI=1S/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m0/s1

InChIKey

KRJLRVZLNABMAT-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@H](CN)NC(OC(C)(C)C)=O

CAS DataBase Reference

73259-81-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-Dap-OH Usage And Synthesis

Chemical Properties

White powder

Uses

Reactant for:

• Protein assembly directed by synthetic molecular recognition motifs
• Solid phase synthesis of gramicidin S cyclic analogs with antibiotic and hemolytic activities
• Synthesis of HCV protease inhibitor modified analogs
• Solid phase synthesis of peptidic V1a receptor agonists
• Directed peptide assembly at lipid-water interface

Uses

(S)-3-amino-2-(tert-Butoxycarbonylamino)propionic acid (Boc-Dap-OH) is a derivative of amino acids, mainly used as an intermediate in organic synthesis and pharmaceutical chemistry, and can be used in the synthesis of peptide drug molecules and bioactive molecules.

Preparation

The raw material was dissolved inabsolute ethanol (5 mL), and the reaction flask was immersed in a water bath at 25 C. To the alcoholicsolution, 10% palladium-carbon (22.9 mg) and 1,4-cyclohexadiene (10 equivalents with respect to4; 0.47 mL, 5.0 mmol) were added, and the mixture was allowed to react under magnetic stirringovernight. After filtration over a short pad of Celite 545, the solvent was evaporated under reducedpressure conditions, and the solid residue was partitioned in a 1:1 (v/v) H2O/EtOAc mixture (10 mL).The aqueous phase was separated, back extracted with EtOAc (3 10 mL), concentrated under reducedpressure conditions, and lyophilized.Finally, the target product Boc-Dap-OH is obtained.

Definition

Boc-Dap-OH is an amino acid molecule that is a zwitterion. Therefore, the addition of a base is required to prepare a nucleophilic amino acid. It is commonly acts as a nucleophile to attack the acyl carbon.

Boc-Dap-OH(73259-81-1)Related Product Information

• Cbz-beta-Amino-L-alanine
• (S)-1-N-BOC-4-N-FMOC-PIPERAZINE-2-CARBOXYLIC ACID
• (S)-N-1-Boc-N-4-Cbz-2-piperazine carboxylic acid
• (S)-4-Boc-Piperazine-3-carboxylic acid
• Boc-Dap-OH
• (S)-1-N-Boc-piperazine-2-carboxylic acid methyl ester
• 2,3-Diaminopropionic acid
• L-2,3-Diaminopropionic acid
• BOC-DAP(DNP)-OH
• BOC-L-DPA(BOC)-OH
• BOC-DAP(FMOC)-OH
• BOC-AZA-L-LEUCINE
• BOC-ALBIZZIIN
• BOC-BETA-N-BENZYLAMINO-L-ALA
• BOC-DAP(DNP)-OSU
• BOC-DAP(ALOC)-OH DCHA
• BOC-DAP(BOC)-OH DCHA
• BOC-DAP(ALOC)-OH