Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

714151

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

product name

Fmoc-β-azido-Ala-OH, ≥98.0% (HPLC)

Quality Level

100

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

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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Triazole phosphohistidine analogues compatible with the Fmoc-strategy.
McAllister, Tom E and Webb, Michael E
Organic & Biomolecular Chemistry, 10(20), 4043-4049 (2012)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service