Clazamycin b

Catalog Number	ACM71774497-1
CAS Number	71774-49-7
Synonyms	(2S,7aS)-2α-Chloro-2,3-dihydro-5-imino-1H-pyrrolizin-7aα(5H)-ol
IUPAC Name	(2S,8S)-2-chloro-5-imino-2,3-dihydro-1H-pyrrolizin-8-ol
Molecular Weight	172.61
Molecular Formula	C7H9ClN2O
InChI	InChI=1S/C7H9ClN2O/c8-5-3-7(11)2-1-6(9)10(7)4-5/h1-2,5,9,11H,3-4H2/t5-,7+/m0/s1
InChI Key	DVCHIDKMDZZKBR-CAHLUQPWSA-N
Purity	95%+
Complexity	241
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	2
Exact Mass	172.0403406
Heavy Atom Count	11
Hydrogen Bond Acceptor Count	2
Hydrogen Bond Donor Count	2
Isomeric SMILES	C1[C@@H](CN2[C@]1(C=CC2=N)O)Cl
Monoisotopic Mass	172.0403406
PhysicalState	Powder
Rotatable Bond Count	0
Topological Polar Surface Area	47.3 Ų

Case Study

Interconversion of the Antitumor Agent Clazamycins A and B

Douglas D. Buechter, et al. J. Nat. Prod. 1987, 50, 3, 360-367.

Clazamycin, a novel pyrrolizidine antitumor antibiotic, exists in aqueous solution as a mixture of two epimers, clazamycins A and B, the ratio ofwhich is pH dependent. This work studied the interconversion of clarazamycin A and B, showing the azacyclooctenone species [3] as an intermediate in the interconversion process.
Interconversion mechanism of clazamycins A and B
· In aqueous solution clazamycin exists as a mixture of two diastereomers, clazamycins A and B [1A, 1B], epimeric at C6a, with the A isomer predominating (62%) at neutral pH.
· Based on Dreiding models, there may be a negative steric interaction between the C5 chlorine and C6a hydroxyl when they are located on the same side of the five-membered ring in the B isomer. This could explain the ratio that was observed. The conversion of the two isomers can happen in two ways: either through the formation of an iminium ion [2] by removing the C6a hydroxyl, or through the opening of the ring to create an azacyclooctenone [3].
· Results based on 1H nmr and optical rotation studies suggest azacyclooctenone species [3] as intermediates in the interconversion process.

Custom Q&A

What is the chemical name of clazamycin B?

The chemical name of clazamycin B is (2S,7aS)-2α-Chloro-2,3-dihydro-5-imino-1H-pyrrolizin-7aα(5H)-ol.

What is the molecular formula of clazamycin B?

The molecular formula of clazamycin B is C7H9ClN2O.

What is the molecular weight of clazamycin B?

The molecular weight of clazamycin B is 172.61.

What is the CAS number of clazamycin B?

The CAS number of clazamycin B is 71774-49-7.

What is the boiling point of clazamycin B?

The boiling point of clazamycin B is predicted to be 295.8±50.0 °C.

What is the density of clazamycin B?

The density of clazamycin B is predicted to be 1.60±0.1 g/cm3.

What is the pKa value of clazamycin B?

The pKa value of clazamycin B is predicted to be 9.77±0.40.

What is the chemical structure of clazamycin B?

The chemical structure of clazamycin B is a 1H-Pyrrolizin-7a(5H)-ol, 2-chloro-2,3-dihydro-5-imino-, with the stereochemistry (2S,7aS).

What are the synonyms of clazamycin B?

Some synonyms of clazamycin B are clazamycin B and (2S,7aS)-2α-Chloro-2,3-dihydro-5-imino-1H-pyrrolizin-7aα(5H)-ol.

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