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15380

Sigma-Aldrich

Boc-Ala-OH

≥99.0% (TLC)

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Synonym(s):
N-(tert-Butoxycarbonyl)-L-alanine, Boc-L-alanine
Linear Formula:
CH3CH[NHCO2C(CH3)3]CO2H
CAS Number:
Molecular Weight:
189.21
Beilstein:
1726365
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:

Quality Level

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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This Item
35965348991315549
Boc-Ala-OH ≥99.0% (TLC)

Sigma-Aldrich

15380

Boc-Ala-OH

Boc-Ile-OH 98%

Sigma-Aldrich

359653

Boc-Ile-OH

Boc-Ala-OH-15N ≥98 atom % 15N, ≥99% (CP)

Sigma-Aldrich

489913

Boc-Ala-OH-15N

Boc-N-Me-Ala-OH ≥99.0% (TLC)

Sigma-Aldrich

15549

Boc-N-Me-Ala-OH

optical activity

[α]20/D −25±1°, c = 2% in acetic acid

optical activity

[α]20/D +2.7°, c = 2 in acetic acid

optical activity

[α]20/D −23°, c = 2 in acetic acid

optical activity

[α]20/D −30±1°, c = 1% in ethanol

mp

79-83 °C (lit.)

mp

66-69 °C (lit.)

mp

79-83 °C (lit.)

mp

-

functional group

amine, carboxylic acid

functional group

amine, carboxylic acid

functional group

Boc

functional group

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

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

reaction suitability

-

reaction suitability

reaction type: Boc solid-phase peptide synthesis

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

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A facile one pot route for the synthesis of imide tethered peptidomimetics
Panduranga V, et al.
Organic & Biomolecular Chemistry, 14(2), 556-563 (2016)
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)
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)
Leila Quercini et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(1), 192-207 (2020-01-10)
The peptide sequence KKIRVRLSA was synthesized in a dimeric structure (SET-M33DIM) and evaluated as a candidate drug for infections due to multidrug-resistant (MDR) Gram-negative pathogens. SET-M33DIM showed significant antibacterial activity against MDR strains of Klebsiella pneumoniae, Acinetobacter baumannii, and Escherichia
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

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