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287067

Sigma-Aldrich

L-Proline methyl ester hydrochloride

98%, for peptide synthesis

Synonym(s):

(S)-Methyl pyrrolidine-2-carboxylate hydrochloride, L-Pro-OMe HCl

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2 · HCl
CAS Number:
2133-40-6
Molecular Weight:
165.62
Beilstein:
3596045
EC Number:
218-363-0
MDL number:
MFCD00012708
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24857264
NACRES:
NA.22

product name

L-Proline methyl ester hydrochloride, 98%

Quality Level

100

Assay

98%

form

solid

optical activity

[α]20/D −31°, c = 0.5 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

69-71 °C (lit.)

application(s)

peptide synthesis

SMILES string

Cl[H].[H][C@]1(CCCN1)C(=O)OC

InChI

1S/C6H11NO2.ClH/c1-9-6(8)5-3-2-4-7-5;/h5,7H,2-4H2,1H3;1H/t5-;/m0./s1

InChI key

HQEIPVHJHZTMDP-JEDNCBNOSA-N

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Application

L-Proline methyl ester hydrochloride can be used as:
  • A building block in peptide synthesis.
  • A catalyst to synthesize 3,4-dihydropyrimidin-2-(1H)-ones via Biginelli condensation reaction with aryl aldehydes, methyl acetoacetate, and urea.
  • A reactant to prepare prolylproline.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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
STBL2775
STBL2249
STBK9405
STBK5955
STBK2938

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Studies on the Biginelli reaction: a mild and selective route to 3, 4-dihydropyrimidin-2 (1H)-ones via enamine intermediates
Mabry J and Ganem B
Tetrahedron Letters, 47(1), 55-56 (2006)
An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions
Thajudeen H, et al.
Tetrahedron Letters, 51(9), 1303-1305 (2010)
Synthesis of Prolylproline
Gaidukevich VA, et al.
Russ. J. Org. Chem., 55(7), 1005-1008 (2019)
Ernest Mordret et al.
Molecular cell, 75(3), 427-441 (2019-07-30)
The translation machinery and the genes it decodes co-evolved to achieve production throughput and accuracy. Nonetheless, translation errors are frequent, and they affect physiology and protein evolution. Mapping translation errors in proteomes and understanding their causes is hindered by lack
Emily M Christensen et al.
The Journal of biological chemistry, 295(52), 18316-18327 (2020-10-29)
Pyrroline-5-carboxylate reductase 1 (PYCR1) catalyzes the biosynthetic half-reaction of the proline cycle by reducing Δ1-pyrroline-5-carboxylate (P5C) to proline through the oxidation of NAD(P)H. Many cancers alter their proline metabolism by up-regulating the proline cycle and proline biosynthesis, and knockdowns of

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