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15380

Sigma-Aldrich

Boc-Ala-OH

≥99.0% (TLC)

Synonym(s):

N-(tert-Butoxycarbonyl)-L-alanine, Boc-L-alanine

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About This Item

Linear Formula:
CH3CH[NHCO2C(CH3)3]CO2H
CAS Number:
15761-38-3
Molecular Weight:
189.21
Beilstein:
1726365
EC Number:
239-847-8
MDL number:
MFCD00037225
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57647398

Quality Level

100

Assay

≥99.0% (TLC)

optical activity

[α]20/D −25±1°, c = 2% in acetic acid

reaction suitability

reaction type: Boc solid-phase peptide synthesis
reaction type: C-H Activation
reagent type: ligand
reaction type: Peptide Synthesis

mp

79-83 °C (lit.)

application(s)

peptide synthesis

functional group

amine
carboxylic acid

SMILES string

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

InChI

1S/C8H15NO4/c1-5(6(10)11)9-7(12)13-8(2,3)4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m0/s1

InChI key

QVHJQCGUWFKTSE-YFKPBYRVSA-N

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Application

Boc-Ala-OH can be used:
  • In the preparation of N-propargylalanine, a key precursor to generate N-(3-aryl)propylated alanine residues.
  • In the resolution of racemic mixture of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol.
  • In the one-pot synthesis of hybrid tripeptidomimetics containing both amide and imide functionalities.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of N-(3-arylpropyl) amino acid derivatives by sonogashira types of reaction in aqueous media
Lopez-Deber MP, et al.
Organic Letters, 3(18), 2823-2826 (2001)
Convenient synthesis and efficient resolution of 3, 3′-bis (benzyloxy)-1, 1′-binaphthalene-2, 2′-diol
Tsubaki K, et al.
Tetrahedron Asymmetry, 14(10), 1393-1396 (2003)
A facile one pot route for the synthesis of imide tethered peptidomimetics
Panduranga V, et al.
Organic & Biomolecular Chemistry, 14(2), 556-563 (2016)
Huang-Han Chen et al.
Analytica chimica acta, 865, 53-59 (2015-03-04)
Polydimethylsiloxane (PDMS) is widely used for microfabrication and bioanalysis; however, its surface functionalization is limited due to the lack of active functional groups and incompatibility with many solvents. We presented a novel approach for in situ fabrication of cleavable peptide
Keyvan Dastmalchi et al.
Journal of agricultural and food chemistry, 63(30), 6810-6822 (2015-07-15)
The cultivation, storage, and distribution of potato tubers are compromised by mechanical damage and suboptimal healing. To investigate wound-healing progress in cultivars with contrasting russeting patterns, metabolite profiles reported previously for polar tissue extracts were complemented by GC/MS measurements for

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