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171824

Sigma-Aldrich

DL-Proline

99%, for peptide synthesis, ReagentPlus®

Synonym(s):

(±)-Pyrrolidine-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
609-36-9
Molecular Weight:
115.13
Beilstein:
80812
EC Number:
210-189-3
MDL number:
MFCD00005250
UNSPSC Code:
12352209
PubChem Substance ID:
24850387
NACRES:
NA.22

product name

DL-Proline, ReagentPlus®, 99%

Quality Level

100

product line

ReagentPlus®

Assay

99%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

208 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)C1CCCN1

InChI

1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)

InChI key

ONIBWKKTOPOVIA-UHFFFAOYSA-N

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General description

DL-Proline, also known as 2-pyrrolidinylcarboxylic acid, is an amino acid commonly used in solution-phase peptide synthesis due to its ability to act as a turn inducer resulting from its restricted phi( ϕ) angle.

Application

DL-Proline can be is used in the preparation of cis-aminoproline-alkene (cis-Apa)linker, which is further used as an intermediate compound for the synthesis of cyclic pseudopeptides via solution phase peptide synthesis.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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cis-Apa: A practical linker for the microwave-assisted preparation of cyclic pseudopeptides via RCM cyclative cleavage
A Baron
The Journal of Organic Chemistry, 76, 766-772 (2011)
Recent Progress in Solid-Phase Total Synthesis of Naturally Occurring Small Peptides
H Yan
Advanced Synthesis & Catalysis, 364, 1934-1961 (2022)
Antoinette Bugyei-Twum et al.
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The Journal of biological chemistry, 290(21), 13440-13453 (2015-04-04)
Lipid A in LPS activates innate immunity through the Toll-like receptor 4 (TLR4)-MD-2 complex on host cells. Variation in lipid A has significant consequences for TLR4 activation and thus may be a means by which Gram-negative bacteria modulate host immunity.
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Although an increasing number of horizontal gene transfers have been reported in eukaryotes, experimental evidence for their adaptive value is lacking. Here, we report the recent transfer of a 158-kb genomic region between Torulaspora microellipsoides and Saccharomyces cerevisiae wine yeasts
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