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Merck
CN

714151

Fmoc-β-azido-Ala-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

(S)-3-Azido-2-(Fmoc-amino)propionic acid, Fmoc-3-azido-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C18H16N4O4
CAS Number:
684270-46-0
Molecular Weight:
352.34
UNSPSC Code:
12352209
PubChem Substance ID:
329763258
NACRES:
NA.26
MDL number:
MFCD11052919

Key Documents

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Product Name

Fmoc-β-azido-Ala-OH, ≥98.0% (HPLC)

SMILES string

OC(=O)[C@H](CN=[N+]=[N-])NC(=O)OCC1c2ccccc2-c3ccccc13

InChI

1S/C18H16N4O4/c19-22-20-9-16(17(23)24)21-18(25)26-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H,21,25)(H,23,24)/t16-/m0/s1

InChI key

ZITYCUDVCWLHPG-INIZCTEOSA-N

assay

≥98.0% (HPLC)

form

lumps

optical activity

[α]/D -10.0±1.0°, c = 1 in DMF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis, reaction type: click chemistry

impurities

15.3-16.5% nitrogen, 60.1-62.5% carbon

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Fmoc-β-azido-Ala-OH chloride is a general N-terminal protected reagent used in the solid phase peptide synthesis. Azido group allows it to undergo copper-mediated click chemistry reactions.
It can be used in:
  • Synthesis of α-N-acetylgalactosamine (α-GalNAc) linked antifreeze glycopeptides (AFGPs).
  • Synthesis of stimuli-responsive multifunctional peptide gatekeepers for drug delivery applications.
  • Synthesis of triazole-linked glycopeptides via Cu(I)-catalyzed 1,3-dipolar cycloaddition (CuAAC).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN2351
BCCM4148
BCCM0257
BCCH7234
BCCF2858

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Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis.
Kuijpers, Brian HM et al.
Organic Process Research & Development, 12(3), 503-511 (2008)
Triazole phosphohistidine analogues compatible with the Fmoc-strategy.
McAllister, Tom E and Webb, Michael E
Organic & Biomolecular Chemistry, 10(20), 4043-4049 (2012)
Stimuli-responsive conformational conversion of peptide gatekeepers for controlled release of guests from mesoporous silica nanocontainers.
Lee, Jeonghun et al.
Journal of the American Chemical Society, 136(37), 12880-12883 (2014)
Synthesis of fish antifreeze neoglycopeptides using microwave-assisted ?click chemistry?.
Miller, Nicole et al.
Organic Letters, 11(11), 2409-2412 (2009)

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