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Merck

531480

Fmoc-Ala-OH

95%, for peptide synthesis

Synonym(s):

N-(9-Fluorenylmethoxycarbonyl)-L-alanine, Fmoc-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C18H17NO4
CAS Number:
35661-39-3
Molecular Weight:
311.33
NACRES:
NA.26
PubChem Substance ID:
24877820
UNSPSC Code:
12352209
EC Number:
252-660-6
MDL number:
MFCD00037139
Beilstein/REAXYS Number:
2225975

Key Documents

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Product Name

Fmoc-Ala-OH, 95%

InChI key

QWXZOFZKSQXPDC-NSHDSACASA-N

InChI

1S/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m0/s1

SMILES string

C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

assay

95%

optical activity

[α]20/D −18°, c = 1 in DMF

reaction suitability

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

mp

147-153 °C (lit.)

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

Quality Level

100

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Application

Fmoc-Ala-OH is commonly used :
  • as a building block in the preparation of triazolopeptides , and azapeptides
  • in the synthesis of bis-cationic porphyrin peptides using the standard Fmoc solid-phase synthesis
  • to transform Mannich-adducts into α-halogenated amides without undergoing aziridination

General description

Fmoc-Ala-OH also known as Fmoc-L-alanine, is a versatile reagent used in Fmoc solid-phase peptide synthesis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5457
SDBB5447
SDBB3534
SDBB0159
STBK8567

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Towards sequence selective DNA binding: design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures
E Biron
Organic & Biomolecular Chemistry, 6, 2507-2515 (2008)
Fabian Schnitter et al.
Nature protocols, 16(8), 3901-3932 (2021-07-02)
Many supramolecular materials in biological systems are driven to a nonequilibrium state by the irreversible consumption of high-energy molecules such as ATP or GTP. As a result, they exhibit unique dynamic properties such as a tunable lifetime, adaptivity or the
? -Halo amides as competent latent enolates: direct catalytic asymmetric Mannich-type reaction
B Sun
Journal of the American Chemical Society, 139, 8295-8301 (2017)
Substrate-derived triazolo-and azapeptides as inhibitors of cathepsins K and S
M Galibert
European Journal of Medicinal Chemistry, 144, 201-210 (2018)
Xue Zhi Zhao et al.
Molecules (Basel, Switzerland), 23(8) (2018-07-28)
HIV-1 integrase (IN) inhibitors represent a new class of highly effective anti-AIDS therapeutics. Current FDA-approved IN strand transfer inhibitors (INSTIs) share a common mechanism of action that involves chelation of catalytic divalent metal ions. However, the emergence of IN mutants
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