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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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD8029V
WXBD3008V
MKCK0615
MKCG7364
MKBZ5402V

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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.
Cardiovascular diabetology, 13, 89-89 (2014-06-03)
Despite advances in the treatment of heart failure, mortality remains high, particularly in individuals with diabetes. Activated transforming growth factor beta (TGF-β) contributes to the pathogenesis of the fibrotic interstitium observed in diabetic cardiomyopathy. We hypothesized that high glucose enhances
Nina Maeshima et al.
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.
Souhir Marsit et al.
Molecular biology and evolution, 32(7), 1695-1707 (2015-03-10)
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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