GB1292846A - A process for the synthesis of leupeptins and their analogues - Google Patents

A process for the synthesis of leupeptins and their analogues

Info

Publication number: GB1292846A
Authority: GB; United Kingdom
Prior art keywords: leu; arg; ome; nov; leupeptins
Prior art date: 1968-11-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

GB54834/69A

Other languages

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Microbial Chemistry Research Foundation

Original Assignee

Microbial Chemistry Research Foundation

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-11-21

Filing date

1969-11-10

Publication date

1972-10-11

1969-11-10 Application filed by Microbial Chemistry Research Foundation filed Critical Microbial Chemistry Research Foundation

1972-10-11 Publication of GB1292846A publication Critical patent/GB1292846A/en

Status Expired legal-status Critical Current

Links

BMGMINKVTPDDRZ-UHFFFAOYSA-N 2-acetamido-n-[1-[[5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide;n-[1-[[5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methyl-2-(propanoylamino)pentanamide Chemical compound CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N.CCC(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N BMGMINKVTPDDRZ-UHFFFAOYSA-N 0.000 title abstract 2
108010011078 Leupeptins Proteins 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title 1
238000000034 method Methods 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract 3
SQGBTKIDTKOYMS-RYUDHWBXSA-N (2s)-2-[[(2s)-2-acetamido-4-methylpentanoyl]amino]-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(C)=O SQGBTKIDTKOYMS-RYUDHWBXSA-N 0.000 abstract 2
SQGBTKIDTKOYMS-UHFFFAOYSA-N Ac-Leu-Leu Natural products CC(C)CC(C(O)=O)NC(=O)C(CC(C)C)NC(C)=O SQGBTKIDTKOYMS-UHFFFAOYSA-N 0.000 abstract 2
SENJXOPIZNYLHU-UHFFFAOYSA-N L-leucyl-L-arginine Natural products CC(C)CC(N)C(=O)NC(C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-UHFFFAOYSA-N 0.000 abstract 2
108010000761 leucylarginine Proteins 0.000 abstract 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
238000005984 hydrogenation reaction Methods 0.000 abstract 1
108010091798 leucylleucine Proteins 0.000 abstract 1
229910052987 metal hydride Inorganic materials 0.000 abstract 1
150000004681 metal hydrides Chemical class 0.000 abstract 1
230000001590 oxidative effect Effects 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

GB54834/69A 1968-11-21 1969-11-10 A process for the synthesis of leupeptins and their analogues Expired GB1292846A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP8482468		1968-11-21
JP8729268		1968-11-30
JP4536969		1969-06-11

Publications (1)

Publication Number	Publication Date
GB1292846A true GB1292846A (en)	1972-10-11

Family

ID=27292208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
GB54834/69A Expired GB1292846A (en)	1968-11-21	1969-11-10	A process for the synthesis of leupeptins and their analogues

Country Status (8)

Country	Link
BE (1)	BE742067A (xx)
CH (1)	CH534131A (xx)
DE (1)	DE1958383C3 (xx)
DK (1)	DK146320C (xx)
FR (1)	FR2023831B1 (xx)
GB (1)	GB1292846A (xx)
NL (1)	NL166923C (xx)
SE (1)	SE369074B (xx)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5754157A (en) *	1980-09-19	1982-03-31	Nippon Kayaku Co Ltd	L-argininal derivative and its preparation
JP2701932B2 (ja) *	1989-04-10	1998-01-21	サントリー株式会社	タンパク質分解酵素阻害剤
DE4207479C2 (de) *	1992-03-10	1994-11-17	Goetze Ag	Wellendichtring zur Abdichtung eines geteilten Gehäuses

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1268212A (en) *	1968-04-19	1972-03-22	Zaidan Hojin Biseibutsu	Tripeptide derivatives

1969
- 1969-11-10 GB GB54834/69A patent/GB1292846A/en not_active Expired
- 1969-11-18 SE SE15817/69A patent/SE369074B/xx unknown
- 1969-11-20 DK DK615169A patent/DK146320C/da not_active IP Right Cessation
- 1969-11-20 FR FR6940289A patent/FR2023831B1/fr not_active Expired
- 1969-11-20 NL NL6917470.A patent/NL166923C/xx not_active IP Right Cessation
- 1969-11-20 DE DE1958383A patent/DE1958383C3/de not_active Expired
- 1969-11-21 CH CH1739169A patent/CH534131A/de not_active IP Right Cessation
- 1969-11-21 BE BE742067D patent/BE742067A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH534131A (de)	1973-02-28
FR2023831A1 (xx)	1970-08-21
NL166923B (nl)	1981-05-15
BE742067A (xx)	1970-05-04
NL6917470A (xx)	1970-05-25
DK146320B (da)	1983-09-05
DE1958383B2 (de)	1974-05-22
DE1958383A1 (de)	1970-06-04
NL166923C (nl)	1981-10-15
FR2023831B1 (xx)	1974-01-11
DE1958383C3 (de)	1974-12-19
SE369074B (xx)	1974-08-05
DK146320C (da)	1984-02-20

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Legal Events

Date	Code	Title	Description
1973-02-21	PS	Patent sealed [section 19, patents act 1949]
1986-07-09	PCNP	Patent ceased through non-payment of renewal fee