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Key Documents

H54409

Sigma-Aldrich

trans-4-Hydroxy-L-proline

≥99%, for peptide synthesis

Synonym(s):

(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein/REAXYS Number:
81441
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

product name

trans-4-Hydroxy-L-proline, ≥99%

assay

≥99%

form

crystalline powder

optical activity

[α]25/D −75.6°, c = 1 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white to off-white

mp

273 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

O[C@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

InChI key

PMMYEEVYMWASQN-DMTCNVIQSA-N

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General description

Trans-4-hydroxy-L-proline is an isomer of hydroxyproline used as a chiral building block in the production of many pharmaceuticals like neuroexcitatory kainoids.

Application

Versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli
Yi Y, et al.
BMC biotechnology, 14, 1-8 (2014)
Synthetic Communications, 23, 2691-2691 (1993)
Tetrahedron Letters, 35, 6163-6163 (1994)
Tetrahedron, 49, 6195-6195 (1993)
Jacob Kofoed et al.
Chemical communications (Cambridge, England), (14)(14), 1482-1484 (2006-04-01)
The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(L-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl)pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of

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